Thoughtexchange Chief People Officer Dessalen Wood

Dessalen WoodThoughtexchange Chief People Officer

Today I’m joined by Dessalen Wood, Chief People Officer at Thoughtexchange. Dessalen has used the Thoughtexchange product to gather deep insights about employee motivations, and has used the data to determine the gap between what employees report is most important in a role, as opposed to which factors actually lead to increased retention and job satisfaction.

Episode Transcript





[00:00:05] RS: Welcome to Talk Talent To Me, a podcast featuring the most elite talent leaders on the front lines with modern recruitment.


[00:00:12] SPEAKER 1: We actually want to understand the themes of someone’s life. We want to understand how they make decisions. Are they willing to take risks? And what it looks like when they fail.


[00:00:22] RS: No holds barred, completely off the cuff interviews, with directors of recruitment, VPS of global talent, CHROs, and everyone in between.


[00:00:29] SPEAKER 2: Once I went through the classes and the trainings and got the certifications through diversity and inclusion, I still felt like something was missing.


[00:00:39] SPEAKER 3: Talent acquisition, it’s a fantastic career. You are trusted by the organization. You get to work with the C suite and the security at the front desk and everybody in between and everybody knows you.


[00:00:52] RS: I’m your host, Rob Stevenson. And you’re about to hear the best in the biz Talk Talent To Me.




[00:00:59] RS: Joining me today for this latest installment of Talk Talent To Me is ThoughtExchange’s Chief People Officer, Dessalen Wood. Dessalen, welcome to the podcast. How are you?


[00:01:07] DW: I’m great, Rob. So grateful to have this opportunity, so thanks for having me on the show. 


[00:01:12] RS: Yeah. I’m so pleased to have the Dessalen. There is precisely one Dessalen on all of LinkedIn, I’m led to believe. The brand is strong for you in 2021. Congrats on that.


[00:01:22] DW: Yeah. Growing up with a different name was challenging, but as an adult, for social media purposes, it’s actually wonderful.


[00:01:28] RS: Isn’t it funny how the things that make you weird as a kid make you awesome as an adult?


[00:01:31] DW: It is. It’s why you don’t let children pick their own names. I now understand that.


[00:01:36] RS: There should be some rules. Yes, exactly. There should be some manner of oversight. But yeah, I love that. I love that there’s exactly one Dessalen, you’re easy to find and it will be easier for the folks out there in the podcast trying to find should they choose to. I’m so pleased you’re here with me today. I have so many things that I want to ask you about. Before we get too deep in the weeds though, I’d love to just set a little context about who you are, and your role at ThoughtExchange. Would you mind telling us a little about, I guess, first ThoughtExchange and then we can get into the Dessalen of it all too.


[00:02:04] DW: For sure. ThoughtExchange is really interesting because it’s a discussion management platform really for scaling conversations with large groups of people or even the small groups of people, where there’s a concern around people being candid or feeling psychologically safe. Essentially, it’s a platform for people to ask an open-ended question, a broad question, narrow, whatever they want, to a group of people and really collect their thoughts on that matter. Then once they share their thoughts, they actually see the thoughts of others and they’re able to rate them for how much they resonate with the person, or how little they resonate out of like a five-star piece. This is something you don’t really need to teach. Everybody uses Yelp, or Amazon or any of these things. It’s reviewing other people’s thoughts.


Then at the end of the exchange, when you’re finished reading, you actually see the results. There’s a lot of transparency involved. Why this is an amazing tool to have is that the person who launches and exchange actually has an extremely detailed dataset on not only the voting preferences of the group, but even trends, or differences or tension that’s in that conversation. They get this really deep insight in a matter of moments, and you can run these either live at a meeting in order to really get to the root cause of the issue before a discussion begins, or you can run it over a course of a couple of days. In essence, visiting your entire organization in a really candid and psychologically safe way in a matter of 72 hours. 


[00:03:23] RS: Okay. It’s almost like running a really nuanced focus group on your – whatever it is, your new company values, your rollouts, your philosophies, whatever it may be?


[00:03:31] DW: Yeah. Feedback on an initiative or even a problem to be solved. Where we see a lot of people assuming, you use the kind of tool like ThoughtExchange, it was to hear from people or to – I hear a lot of people say, “Get buy-in.” But to me, buying is the result of the process you use in order to get to a decision. If you’re using ThoughtExchange early in the decision-making process, you’re actually getting ideas and you’re actually improving the decision that you’re going to make by iterating with a large population because crowds are very, very smart. If you believe in the wisdom of the crowd and you iterate with them, your actual end decision or product or initiative will be stronger as a result of the process you went through. 


[00:04:09] RS: I love how you wound up at ThoughtExchange desk, which is kind of a great testimonial for the company. You were a user of ThoughtExchange. In a previous life, you were a customer and got to know the team, got to know the product and then wound up a full-time employee, right?


[00:04:24] DW: Yeah. It’s actually an interesting story, because I really was not in the software industry at all. I’d been in big box retail in the service industry in HR roles for over 20 years at that point. I was actually at a conference speaking on employee motivation. There was a vendor presentation and Dave MacLeod, who is our CEO, did this really interesting interactive demonstration of the product by launching a question to the crowd with a QR code, and then you could watch all the thoughts going in, and the rating. This was in 2017.


At that point, I did a lot of facilitations, specifically for senior and executive offsites and I used those clickers. You remember clickers? You had them on a lanyard, and you would try to like vote on something from like – yeah, really old school. I’d been trying to find a way to really get genuine conversations going inside offsites, type of thing. I saw the product and it took us to Dave and we decided to try it in my next executive offsite. It was about eight weeks from then. 


I really went in just thinking what would happen if I used this tool. Of course, I used it for a really high value question, which was, the company I was with prior, which is Cineplex Entertainment had been merging and purchasing a lot of different organizations and had grown from two business lines to nine. We had a lot of decision-making bottlenecks.


I asked this question to 80 senior team members. “What are the biggest behavior changes we could do to decentralize decision making from a senior team perspective?” On the screen, I’m seeing thoughts and ideas that you would never see at a roundtable, or at Flipcharts or any of that type of thing. They were provocative, and they were interesting and they were engaging. People were reading a lot. I actually had to put a stop to it, because people were having such a good time reading thoughts. Then, up there I had a dataset, a prioritized dataset of the behavior changes we need to make at the executive team to decentralize decision making. That took, I think, the course from when I launched it to when I closed it about eight minutes. I thought, “This is pretty amazing.”


I actually used the tool then through a webinar to the rest of the company. I went to every business unit and asked the same question, to see, you know, is this a common theme across? Then I rolled out effectiveness program based on the results. I was able to go like from an issue that seem really nebulous to like really concrete ideas, to then creating a business plan that had a buy in because of the transparency of the issue. Everybody saw it. I didn’t have to make a business case for what had to change, because the exchange itself is the business case. It was a pretty transformational moment for me as a people leader.


[00:06:57] RS: Yeah, no kidding. I assume you’re still using it. They use the term dogfooding. I personally prefer drinking our own champagne, to just elicit sort of views on people, organizations and decisions. Is that the case?


[00:07:07] DW: Well, what ended up happening for me as I was the large corporate customer for our corporate business. ThoughtExchange had this very healthy education business. I couldn’t help myself. I’m somebody who likes to play with things, so I would write little comments and feedback on what I would like the tool to be doing. I’ve never actually interacted like that with a provider. But I was sending in points and Dave was really engaged with me of like, “How do you need to use it? How do you want to use it? Why are you asking that question? Why wouldn’t you ask it this way?” We really, together, formed a lot of the use cases for the corporate product, until at one point after going to a couple of conferences to speak about ThoughtExchange as a customer, Dave made an offer to come over as the Chief People Officer, work on our people and culture at ThoughtExchange, which is really important, as well as work with our customers on how to use ThoughtExchange the way I had it as a customer myself.


[00:07:56] RS: I think that’s a sneaky, underappreciated path into a company. You get to work with the team a little bit, right? Like you’re working with their customer success or something. You’re meeting some individuals from the team, you’ve really looked under the hood of the product so you know what you’re getting into, as compared to if you’re just going to join a company from the outside, like you might get like a 30-minute demo or something of the product before you started. But you wouldn’t actually know all the nuts and bolts. Sort of good way to assess a company as opposed to like – a lot of people are like, “Ah! I can take this job. Yeah, the products are okay, but it’s a good job and blah, blah, blah, perks.” That’s why I said you’re a good testimonial because you really saw the product and like, “Okay. I believe in this. This works, I used it, that’s why I want to join the company.”


[00:08:37] DW: Exactly. There’s not a lot of roles I would say, there’s a lot of people roles, especially now, very hot chief people officer, CHR type of roles. But a role where you’re going to actually influence the product roadmap, as well as work with Fortune 1000 people leaders and executives on how to implement this kind of transformational communication. There’s just not a lot of opportunities like that. I felt it was an adventure I couldn’t pass up. Even though I had never considered moving from the kind of blue-chip big box service industry into startup software. This was huge, massive leap for me, but again, an opportunity that is hard to come by in terms of the multifaceted role.


[00:09:21] RS: Yeah. Well, well done on the new gig and being able to influence a product, sounds like it’s a great fit for you. I’d love to just talk a little bit more about the people, kind of where ThoughtExchange is now. We had this whole this great rehiring thing, the great resignation I’m led to believe is a real thing. I haven’t covered it much on this podcast, because I wanted to make sure that it was a real phenomenon and not just something that was like a headline in The Business Insider blog post. What’s your experience been with that? Where are the kind of the ebbs and flows of talent at least with regards to ThoughtExchange?


[00:09:51] DW: ThoughtExchange had a wonderful story of having a very strong group of people from the original startup time. This group had largely very little turnover. Really, we were growing, a high-growth company, we doubled in size since I started in 2019. We were able to hold on to the original group of people who started the company, as well integrate in a lot of people who came from different backgrounds who were able to add with their diversity and with their experience to the initial team that had a lot of knowledge. 


We had a really, I would say, I was sitting in a place of privilege to be in a very, very low turnover business. You have to remember, I come from the service industry where your 100% turnover is normal. I had never seen turnover like 2.5% or 3%. I really felt that we hadn’t really built the kind of resilience that you get in the service industry around departures, which I had learned to lose a lot of people that I loved over a course of my career. 


With ThoughtExchange, what happened is that our voluntary turnover is very low, the culture is very strong. Most people who come to ThoughtExchange are coming because of the purpose of the product, as well as the culture itself. We are a purpose-driven company. What we’re doing is really important I think in the world by bringing a way to have an unbiased and diverse conversation inside large organizations. We really rode that wave for quite a while. Then what ended up happening is because there’s so much movement, especially in the SaaS industry, eventually the wave is going to hit you. Because as more and more positions become open, more and more people become aggressive and they start to target your people. Over time, you’re going to see that increase in movement. It was a surprise and not a surprise at the same time.


I started really being curious about what are the reasons around this? Because you know – what’s the first thing you think, Rob, when some somebody says this person is leaving, the person’s leader will say, “Well, they got this offer they can’t turn down,” or “This place is paying more.” You would always hear that there was like some package the person couldn’t resist even though this was the absolute best place to work up until that dollar sign came in. I’ve been in the long – in the people world, we’ve often said that people don’t start looking for more money. It happens that they get an offer when they’re at a point of dissatisfaction and the money is an easy reason to explain their departure.


I decided to run a ThoughtExchange on LinkedIn, asking people, “What would a company need to do to keep you from quitting?” Like basically, what would make you stay? I titled my post, “Should I stay or should I go?” and I put it out to the world to ask them, “What could we do to keep you? What are the reasons you’re leaving?” It was a really interesting dataset, because say, five to one, the answer first in terms of frequency was flexibility. This is a big concern as we were hearing a lot about the return to work. Everybody was being called back or they were hearing they were coming back. The triggering thing in the exchange was to say, “I want to have flexibility and autonomy.”


What our tool does, which is something really interesting is, just because it was said the most, it doesn’t mean it actually is the most important thing. It’s just the first thing you thought of. When we look at our data, we look at it as how frequently something is said. Definitely flexibility. If you’re thinking of the most frequent answer you’re going to get as to what’s going to keep me here. But when you look at importance, which is the star rating of all the thoughts, the actual graph went from having this peak for flexibility and then all these little small tails for all the other reasons people wanted to stay, to almost a straight line. Essentially, people were rating every reason, even if it only came up once, as equally as important as flexibility.


What that really shows me, because you know, I like to use song titles, is the Queen song, I Want it All and I Want it Now. 


[00:13:37] RS: And I want it now.


[00:13:38] DW: Yeah. It was like, actually, “Flexibility is the first thing I thought, but somebody would say, what about caring leaders? Oh! I’m giving that 4.5 stars. What about culture? I’m giving that 4.5 stars. What about your benefits? I’m giving that 4.5 stars.”


[00:13:51] RS: Another Queen song. I Want to Ride My Bicycle.


[00:13:54] DW: There you go. Everybody wanted, when you think here, there was an idea of culture, and vision, and compensation, and trust, flexibility and leading with care were actually all between 4.2 and 4.3 starts. I’ve never actually seen such a flattening when initially the reaction was flexibility.


[00:14:14] RS: Does that mean that it’s just much more complex and nuanced or does it mean that people really have no idea what they want?


[00:14:19] DW: What I think it is, is something that I’ve discussed with people. It’s market scarcity. Right now, it’s a time of employee empowerment. There’ve been different times and I remember hiring when it was 2008, 2009 when you have 400 applicants for one job and you really didn’t have to invest a whole lot into what you were offering as a company. Because what you were offering was just a job, and people were pretty darn grateful to get it. 


Then we get to this point where there is enough employment across most industries, that I think we can raise the standard of what we wanted. I don’t think we were less desiring of a wonderful work environment in 2008. We just couldn’t push for it because there were not enough jobs. Then you get to the point like now, where people can start to be more demanding because they have the option to look elsewhere. Also, companies are really aggressively marketing their culture. 


The idea of looking around on LinkedIn, or you’re looking around on different articles and posts, you’re seeing all these amazing things companies are doing and you’re kind of looking behind you and you’re saying, “Well, I don’t see that here.” We have this transparent view into so many organizations that I think makes people feel like, “I’m a have, and I’m a have-not.” If I think back into my early career, there was a lot of internal marketing organizations telling employees, “This is the best place to work, you shouldn’t go anywhere else.” But that has to be held up now with actual activities and things you’re doing because I can look around and say, “This isn’t actually the best company. There are better ones out there.” 


I think that this idea of saying, “I want all of these pieces,” is because we’re seeing examples in other organizations of amazing cultures, of benefits, of flexibility and of leaders who are really intentional, as well as the company being purpose driven. I’m thinking, “Why do I have to negotiate?” I’m like the only single person at a party full of people looking for a partner, like there’s no reason why I have to lower my standards right now. I think what I’m seeing here is people really raising the bar of the kind of environments they’re in and they can do it now because there’s that much choice.


[00:16:28] RS: Yes. I love what you said a moment ago about the resiliency around departures, which is to say, what are companies doing to really mitigate churn and mitigate people like voluntarily leaving the company? In the same way as like, oh, the company is doing all this work to broadcast how great their culture is, to prospective candidates, right, get more people in. What are you doing to broadcast that and make it a reality for the people at your company? It’s like that metaphor, they say, “You have to date your wife.” Meaning, like you can’t just like take her for granted. You need to keep bringing your A game all the time.


I’m curious, what that has looked like at ThoughtExchange, when it comes to like, how do we survey, how do we understand what it is people actually want and make sure that we’re delivering it to them? It’s sort of related to this question of like, people want all of these things across the board, how do we take that and point it at our own employees to make sure that we’re catering to that?


[00:17:23] DW: That’s a great lead in. Initially, I had this dataset, which is really great for me to be working with their customers as well as talking in social media about what people want in terms of retention. When it came to our population, I actually had to run the same exchange question internally, because we are a remote company. Flexibility will not even be one of them because we have flex time and we’re all remote. I ran the same Exchange, and essentially, I ended up with themes. Themes around employee wellness and workload. Themes around culture. Themes around career growth and things around compensation or total rewards. I ended up with these four buckets of the things that people were looking for in terms of our environment.


Then you have to do a really honest audit of really, how competitive are you? Because most organizations make fairly, I’d say, broad statements without a whole lot of support around how we are competitive with the market, or we pay at market, or we pay above market. But really, what does that actually mean when you look at the conditions in these four separate buckets? What I did is start to do a review as to who can we impact all of these are at the same time back to the, “I want it all and I want it now.” How can we address feelings around workload and wellness as well as compensation, as well as culture, and as well as learning and development? And basically, relaunch some of our really good, I call them retention strategies.


Most employer brand is based on attraction. You’re putting it out there to get people, but you’re not necessarily talking to the people inside. Think of it like phone plans. The big joke is, if you’re new to a plan, you get a great deal, but the person who’s been there three years is paying twice as much as you are. Yeah, a lot of people’s employee experiences like that too. Like existing people don’t see these benefits or they’re not even hearing about them. This idea of remarketing what you offer I think is important. One of my favorite sayings is, a squirrel is just a rat with good PR. I often think that if we don’t package things and talk about them, we can’t assume that they’re top of mind. But when you’re actually looking at it at another company’s website or hearing from the recruiter, they’re telling you things that we actually might be offering in a very competitive way. But you haven’t heard about them, or you haven’t visited an internet site in years and don’t know about that. 


I think this idea of marketing internally what you do, sharing what you do and also being honest when you’re not competitive really and raising your game. Doing that scan of who, if you’re in an enterprise company, what are enterprise business is offering, what are mid-markets, what are startups? And remaining competitive in that area. I don’t think it’s realistic for an enterprise to necessarily show the same culture or benefits as a startup or vice versa. But knowing that you actually are competitive or a leader in those areas I think will give you the confidence to talk to your employees about the true benefits of remaining where they are.


[00:20:13] RS: Yes. Going back to the straight line across all of the rankings. I understand the economic argument, like when there’s a time of lots of jobs, people are like, “Oh! I can’t have it all.” It’s not just that, “I wish I had it, but like that’s a realistic outcome for me as opposed to a time of economic downturn. I just need a job. I just need payroll to run every two weeks and I’ll be grateful.” But that can’t be the case, even when an employee is like, “Oh! I want everything,” surely, there are a couple main things that people actually make their decisions on, whether it’s to join a company or whether it’s to not leave the company they’re at. Do you think there is a discrepancy between what people report is important to them about a role versus what is actually the case?


[00:20:59] DW: Yeah. I think if you look back in time, those reasons are probably going to be different. If I think of when I began was how far the office is from your home. I mean, that sounds probably really old right now and along the lines of, how stable is the company? and also likely some growth opportunities. If I look at what people are looking for now, I think it definitely has changed to more around the quality of your day-to-day work experience. I think the idea of trust and autonomy is a much bigger factor than it was several years ago. 


I’ve done tons of different sort of facilitations, where if you ask people, “What’s the worst trait a leader can have?” And micromanagement outweighs every other trait. I think the idea of being controlled is one of the biggest reasons why people will leave an organization and if they have a lot of autonomy, why they’ll stay. I don’t think you necessarily think of that in the moment. You just think, “I’m unhappy and I was happy there.” But actual happiness often is linked to autonomy and unhappiness is linked to feeling controlled.


I think for me, that was probably the biggest piece, and then there’s the piece of feeling valued and recognized. Valued in terms of you’re being valued for what you do and also the work you do is being valued. “Is my work being valued and am I valued as a person?” I think these are really traditional levers that are so important to us as human beings. Because you know, we haven’t had a major software update in our brain for 70,000 years. The things that have mattered to us still matter to us. I think that having free will as well as having a sense of purpose, and also a sense of being cared for, and then you have those things, I think they’re very hard to give up. When you don’t have them, it’s almost impossible to be happy.


[00:22:49] RS: Yeah. Wow! That’s really profound. It aligns directly to what you’re saying though about how relative it is to economic downturn. Because in a time where it’s really competitive, like you were using ’08, ’09, 400 applicants for one job. Those people just need a paycheck, just need a job, need anything, right? Then in times where there’s just an abundance overall, now, we’re creeping our way up Maslow’s hierarchy of needs a little bit. Now it’s less about, “How do I pay my bills?” and more about like, “Yeah! But how do I feel fulfilled? How do I express myself? How do I realize that self-actualization that is like me as my best self?” Is that too much to ask for a company to have to help you figure out self-actualization for yourself or is that now part of the deal?


[00:23:31] DW: This is a really great point to bring up, Rob. Because I think that a lot of leaders find it – it’s the hardest to be a leader now than it has ever been in most people’s careers. Because the demands on leaders to look at your overall psychological wellness, your career growth, even your at-home situation. Are you safe? Are you healthy? Are you supported? At the same time, we still have deadlines to meet and we have work to do. But the work that you do, you want it to be meaningful, you want the person to feel like they’re contributing to something bigger. 


For a person in a leadership position, I’m sure that that bar graph that I described is not news to them because they’re already feeling that pressure in terms of what leaders are being asked to do. I think when I look at this equation, I often call it the-from-and-for equation. Which is, we’re asking a lot from people right now at work. If you’re a frontline worker, we’re asking you to put yourself at risk and to work often on nights, and weekends and have a whole lot of different demands made on you for that kind of work. If you’re what we call necessarily the knowledge worker, you’re being asked to work – your workload has increased exponentially. There’s no longer anybody who backfills anybody’s role. There’s no such thing as a day off or vacation. There’s just your work waiting for you and piling up.


We have this really big demand for works in terms of what they’re expected to give, what we want from them. They’re looking at the equation of, “What are you going to do for me?” I call it the from-for balance, which is like, “If I’m going to do this much for you in terms of workload or endangering myself, or giving up any work-life balance, what are you going to be giving me for that?” I think when people initially join the company, they underestimate what the company wants from them, and they might overestimate what there is for them there. When they get there, and they’re like, “Oh! Wait! This environment doesn’t have all the things that I expected, and the demands are higher, I’m now out of whack for what I joined for,” and that’s where dissatisfaction lives in that gap between the two.


With organizations, I think there’s two things you can do. It’s not necessarily just give everybody more money because the market is really hot. It looks at all the thing that you can do for someone, which are all the different buckets that I got from this Exchange, and really decide where we’re going to play a really strong game, so that people can start to feel that there’s more balance there, because it’s not realistic for a lot of smaller brands to compete necessarily on compensation alone. But we also know that when people go to a job, they’re excited about the compensation, and often, within a year later, they’re frustrated with the demands of the job for that level of compensation.


I think that as organizations and me as a Chief People Officer, I’m really trying to look across the whole plane and not get sucked into that this is totally a compensation matter. Because I think that largely excuses leaders and organizations from looking at that balance with a very critical eye.


[00:26:23] RS: I feel as though you could run the from-or-for activity on any interpersonal relationship you have, right? The discrepancy is really interesting too. That is where the dissatisfaction is. I think if you were to be honest with yourself as a people leader, as a recruiter, about what that looks like for any given candidate or employee, that’s kind of your employer value proposition right there. This is sort of all the pluses and minuses. This is kind of where you net out, feeling about what you give and take from this relationship.


[00:26:54] DW: Yeah. I think that if you can transparently discuss all the benefits, but also some of the challenges that the business is facing right now because businesses face different challenges at different times. I’ve been in legacy businesses where the challenge is really complacency. Then what happens is disruption. That because you’ve been complacent in your business model, you’re not agile or able to pivot when disruption comes. Disruption comes for every legacy business. That’s that challenge. It’s really, if you are recruiting there, you’d want to explain that to people.


In a startup environment or high growth, you want to talk about the challenges of constant change, and what does that look like, and what is that going to feel like? I think when people feel like you’re really leveled with them about all the benefits and the challenges, when they hit the challenge, they don’t feel like they’ve discovered something that you misled them about. They’re like, “Oh! This is it.” I can give you an example I had years ago. When I was being interviewed for my past role, I was being interviewed by the team who was going to report to me. They asked the classic question, “What kind of leader are you?” Your temptation is to say, “I am supportive, and participative, and motivating and I give you freedom.”


[00:28:05] RS: Yeah. Have you seen Braveheart?


[00:28:07] DW: Exactly. I basically said all the wonderful things that I think I am. Then I said, “And now I’m going to tell you what’s not good about me as a leader. I don’t have a lot of attention to detail. I’m not a process-driven person. I have a lot of ideas that I want to implement, of which you will receive with no real plan on how to do it. The high part, the wonderful part about me is we’re going to have a wonderful colleague-like, very respectful relationship. The downside is that, when I want to do something new, you’re going to be extremely frustrated with me, and you’re going to have to like pin me down to get directions. Because it’s not going to come from me naturally.”


Later on, I was facilitating with this director who I’ve hired and I told that story, somebody raised their hand and they said to him, “How true was that?” Someone said, “It was even worse than she said.” 


[00:28:57] RS: She still white-washed it.


[00:28:58] DW: Yeah. He was like, “I kind of downplayed it at the time because I love autonomy. But oh my God, I couldn’t get a process out of this person if her house was burning down.” I think what was really interesting is you saw this sort of wonderful relationship we had because we started it so honestly. I told the team, “You’re going to have to call me on this and it’s going to be hard, and there’s other points where you’re going to think I’m the best boss you ever had, I’m both.” I think that if organizations presented themselves that way, we would have less people feeling that there was some level of deception during the whole process of being onboarded. 


[00:29:33] RS: You hear people talking about doing that from the company side, it’s like, “Let’s be really realistic and honest about the challenges of this role because people are going to find out.” When the honeymoon phase wears off and it’s just a random rainy Tuesday, nine months down the road, that sheen has worn off, are they going to be able to keep plugging away? It’s a little trickier from the point of view of a candidate though, because you really are trying to put your best foot forward. You don’t want to admit that you have any flaws, you want to be perfect because you want the job. You want to be like, “I’m the perfect fit for this. You need to hire me.”


That, I mean, there’s a tipping point, because in your case where you are very honest about some of your shortcomings, that engenders trust. Like, “Okay, Dessalen has self-awareness. She’s been critical about where she’s lacking. She’s taken feedback or she’s always reflected on herself.” Where do you think that line is between beating yourself up but not like just laying out all of your flaws to the person you want to give you a lot of money?


[00:30:30] DW: What’s an interesting thing is that, I think the idea that you understand your weaknesses and you found ways in order to support those – to work around them, essentially. In my view, the kind of people I tend to hire or to select even from the internal candidate pool are people who are process driven and people who think in a project management mindset because I really lean into that. Even though I know there’s going to be friction between the way I am as an ideas person, as a concept person, and then this person sort of can feel like they’re always popping my balloon with like, “Well, okay. Let’s talk through how we’re going to do it. Let’s put a project line together.” But I surround myself with that kind of person to get that kind of balance.


I think when you’re going to a leadership role, if you’re able to say, “This is what I’m really good at. This is what I don’t naturally tend towards, and this is likely the kind of team I’m going to have to build around that, or the skillset I’m really going to have to nurture on the team.” I think people feel it’s not dangerous. Self-awareness without any self-management is irresponsible. Self-awareness with the ability to manage what you’re aware of, that’s actually a tremendous strength. I think that that’s what I’m looking for for people. Somebody says to me, “When I’m stressed, I can get a little bit snappy.” What I’m waiting for is, “So this is what I’ve done to work around that,” or, “This is how I’ve managed to do this in a way that isn’t disruptive for people.”


I’m not really a huge fan of candidates or internal people displaying all their weaknesses as it’s like, “Now, look at me, I’m so strong and vulnerable because I’ve shared what’s wrong.” I then want to find out what the work around was, because really, for every kind of weakness, you can find a complementary strength in someone else to balance that out, or in a system, or in a software or something that’s going to ensure that that weakness doesn’t poison the work and the people around you. 


[00:32:14] RS: Yeah. That is such a good point. That’s why I was – people at home can’t see but I was snapping my encouragement as if we’re at like a slam poetry reading or something. What did you say? That self-awareness without self-management is irresponsible. Yeah. I would say, it’s even like destructive. You come across this everywhere in your life. It’s like, people who are aware of their flaws and they act like being aware of it is enough. It’s like, “No, no. You also are supposed to do something about it. You have to point that self-awareness somewhere.” It also goes to show you like the really common interview question, “What is your greatest weakness?” People aren’t asking you to beat yourself up. What they’re looking for is, “How have you solved something? How have you identified something where you are deficient and what have you done to overcome it?” That’s what they’re looking for, as opposed to just like, “Well, I sleep in late, and I turn off my alarm and I roll over and looked at my phone for 45 minutes.” That’s not what we’re looking for. It’s like, they want the solution.


[00:33:09] DW: I think there’s a far more openness for people to talk about what they’re strong and what they’re weak in, but there’s still a tendency you say, to want to market yourself a certain way. I think when I’m asking people in an interview to really share some of the areas where they need to improve, the question I use is, “If you could time travel back in time, like a video cassette that you’re rewinding, and you could undo one thing you did, biggest mistake, what is it?” It’s an interesting thing because people will be like, you’ll see the candidates that I tend to prefer are the ones who are like, “There’s that one. There’s that one.” 


[00:33:46] RS: [Inaudible 00:33:46] 


[00:33:48] DW: They’re like, “Okay. I got a story for you.” They literally regale you with the worst thing that they ever did. I find that that kind of ability to have humor, and to reflect, and to have an inventory of all the things I wish I could have done differently shows me that they have a growth and a learning mindset. A person who I can see is trying to curate something for me scares me a lot more than somebody who can’t decide which of the mistakes or disasters to share, because I really feel like that person is constantly revisiting and reviewing things that they did in order to become better, should that situation come up again.


[00:34:25] RS: Could I give you my answer and you can tell me what you read for me as a professional from it?


[00:34:31] DW: Yes. 


[00:34:32] RS: First things that come to mind are like, oh, well, there are all these different career moves I could have made. I could have probably got a job at Coinbase in 2014 and gotten all of my compensation in Bitcoin, and I’d be podcasting from the helipad of my yacht right now, you know? That’s like the obvious one. There’s like some interpersonal stuff, but this isn’t a really satisfying answer, but I’m very privileged that I haven’t had like lots of really catastrophic things happen to me. I look at all of my decisions as kind of like leading me to where I am now. Where I am now is somewhere where I’m really happy, like I do really do love my job and where I live and my partner and my relationships. I worry about butterfly effect, like if I videotaped backed and changed decisions, would I be somewhere else? Would that somewhere else necessarily be better than where I am right now? I don’t know if I would take that risk.


[00:35:20] DW: I’m a huge Sci-Fi fan, so I love the butterfly effect. I think maybe I didn’t phrase it in the way, it’s not necessarily a life decision, it’s like a mistake you made in your work, or something that you did that had an impact, that you didn’t foresee, that you really regret. It’s this idea that everyone’s intention, nobody wakes up in the morning and thinks, “I’m going to do something that’s going to devastate Rob.” I would say, there’s probably four people I’ve met in my entire career who do wake up and think that. The rest of us don’t. It’s this thing, is that, but when you can acknowledge that something you did, a decision you made or didn’t make, an action you took or that you decided not to, had an impact that was so big on the business, or on a person, or on a project. And that you kind of like get this sort of feeling of ache and regret whenever you think about it. I think that that’s somebody whose awareness is driving them to not do that again. 


I think that’s really what I’m looking for when I’m looking for somebody who is growth-mindset oriented as well as humble. Because to me, humility and flexibility are close cousins. It’s very hard to be flexible and adaptable to things that are happening to you if you are not humble. Because if you lack humility, you think you’re always right. If you think you’re always right, I say, certainty is the sickness that many executives suffer from. What I’m looking for when I’m talking to people, and I interview a lot of senior people, is the sense of humility for the decisions they’ve made and for the impacts that they’ve had.


[00:36:49] RS: Okay. Yeah. That makes a lot more sense. I have lots of career examples of that, like little decisions or little things I made. That makes more sense than me going into, “Do I want to be alternate reality Rob?”


[00:37:01] DW: For sure.


[00:37:03] RS: I realize, oh yeah, this is an interview. This isn’t like my own personal episode of Rick & Morty. That makes all the sense in the world. You’re looking for humility, you’re looking for the times people like learned, like learned something like, “Okay. I learned via experience. I learned via the mistake I made, via the trial and error of that and now I’m better for having that.” That makes all the sense in the world to me.


[00:37:22] DW: It’s interesting, we talked about this resignation piece, is that when the talent pool is really – the market is tight, you’re so excited to find one or two candidates that meet the basic requirements for the job, you’re probably less likely to have a conversation like we’re having right now. Because in there, all you want is to confirm that this person is the right person and you’re just so excited that you might be able to fill that position, especially if you’re having scarcity of candidates. I think that what I am concerned about now with all these reshuffles, is that we’re not doing the diligence from an employer employee perspective in these interviews because we are so excited to find a candidate, and that candidate has become enamored with what they believe they’re getting from that organization from the social media or your website.


What I think we want to make sure we’re doing no matter what the market is, is this kind of really deep connection between, what are the challenges and the benefits to the company and what are the strengths that you have and what are some of the opportunities? Are we at the right place and at the right time for each other, regardless of what’s going on in the market? My concern is that we’re going to lose some of that clarity, because once there’s a panic that sets in, we stop thinking with our highest executive function and we start thinking very emotionally. I think the kind of conversation we just had is the ones we want to make sure people are still having even in this hot market.


[00:38:46] RS: Yes. Des, this has been so fascinating chatting with you today. This has been jam packed with insight and you are just so knowledgeable and interesting to listen to. Thank you so much for being a part of the podcast and sharing with us today. I really loved chatting with you.


[00:38:58] DW: Well, thank you Rob and thank you for pushing me to some provocative areas. This was a really interesting and exciting conversation. I enjoyed myself very much so thank you.


[00:39:06] RS: Was this provocative?


[00:39:08] DW: Yeah. It was different from what I’m – when we talk about what it’s like to hire people and what it is that we’re looking for with people, I feel like we keep ourselves largely at the surface of, what are the skills, and what are the demands of the job? As if like all these other nuanced factors are not going to be what’s the downfall of this relationship. I love that we actually didn’t really talk about like the skills or job descriptions and really just talked about where people are at, what do they need and can you give it? I think that fundamental question should be answered in the same level of interest as we look at the actual skills or job experience, so I think you really got me thinking.


[00:39:47] RS: Well, I don’t think we’re going to find a better bookend than you praising me. Let’s call it a podcast. Des, this has been a delight. Thank you one more time for being here and thank all of you out there in podcast land for tuning in. One more time, I have been Rob Stevenson, Dessalen Wood has been Dessalen Wood and you’ve all been amazing, wonderful, talent acquisition darlings. Have a spectacular week and happy hunting.




[00:40:12] RS: Talk Talent To Me is brought to you by Hired. Hired empowers connections by matching the world’s most innovative companies with ambitious tech and sales candidates. With Hired, candidates and companies have visibility into salary offers, competing opportunities and job details. Hired’s unique offering includes customized assessments and salary bias alerts to help remove unconscious bias when hiring.


By combining technology and human touch, our goal is to provide transparency in the recruiting process and empower each of our partners to employ their potential and keep their talent pipeline full. To learn more about how we can help you find your next great hire, head to