Chris Dyer on Remote Leadership (Scaling Tech Podcast Ep17)

Apr 4, 2023 | Developers, Team Management

Chris Dyer is an international keynote speaker, consultant, and a best-selling author for today’s work world, who inspires his audiences with straightforward delivery, insightful candor, and engaging humor. He is author of “The Power of Company Culture” and his most recent book, the Amazon bestseller “Remote Work” with co-author Kim Shepherd. Chris provides public speaking, online courses, and coaching on leadership. He speaks with us in this episode about “Remote Leadership.”

If you’re leading a remote or hybrid team, then make sure you catch this episode to learn from the expert advice Chris shared with us!

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Show notes with links to jump ahead are below

Show Notes from Episode 17 – Chris Dyer on Remote Leadership
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  • 00:00 In the opening quote, Chris talks about how good leadership requires being a mentor to your lowest and your highest performers, but that the people in the middle generally just need you to get out of their way.
  • 00:45 Arin and David introduce the episode with Chris, where Arin notes today’s episode is most focused on leadership in remote teams, which is different than just working in a remote team. Arin notes that he’s probably falling into the trap of trying to mentor people in the middle, which Chris does not recommend and will discuss further in this episode. For David, he notes that he was skeptical initially about the claim by Chris that remote work is a way to discover who the best people are in an organization, and that remote work will make you a better leader and team member. David feels that remote work is not for everyone though, but Chris made a compelling argument that remote work can help a team to better grow and learn.
  • 03:58 Arin introduces Chris Dyer as an international keynote speaker, consultant, and a best-selling author for today’s work world, who inspires his audiences with straightforward delivery, insightful candor, and engaging humor. He is author of “The Power of Company Culture” and his most recent book, the Amazon bestseller “Remote Work” with co-author Kim Shepherd. Chris provides public speaking, online courses, and coaching on leadership. He’ll be speaking with us today about “Remote Leadership.”
  • 04:30 We start with a bit more on Chris’ background and how he got into culture consulting. Chris previously owned a company that did some pretty boring work – background checks. After some encouragement from others, Chris started podcasting about something he found more interesting – team culture. Chris had been reading and studying culture a lot and applying those lessons in the organization of his company, and he started sharing that with others. After selling his company in 2021, he now does consulting and speaking around team culture full time. Chris now most often works with midmarket companies of $5-50M in revenue who are trying to get to the next level.
  • 08:00 Arin asks about at what company sizes do you see a major inflection point? He notes that he and David struggled how to get past 25 people in AgilityFeat at first, but once they figured out how to get to 30 people, it was easy to get to 50. Chris agrees that 25 people is a typical and difficult team size – that’s the size when you first start to have people “get off the bus” because they realize the company is no longer at the size they liked. By the time of 25 employees, you really need a fantastic and experienced leadership team that is reflective of the people you want to hire in the future. That means having more representation in the leadership team, so that you don’t end up with a company of just white men. Once Chris made that change in his company, and he improved his leadership team in many ways, growth started to happen more rapidly and it was easier to recruit new team members. 50-100 people is very messy and unique for every company, and this scale is all about cash flow and deciding if your business is in fact sustainable. Social economists also note that 150 people is the next big moment, that is just as big as the first 25. That’s the point where the CEO cannot know everyone’s names, and now you are more distant from those you hire. Culture becomes more complicated at that point, and the reason many companies automatically start new locations or divisions every time they reach more than 150 people in a specific group.
  • 13:05 Arin asks about a claim that Chris makes in his book, that remote work is actually better for leadership. Chris explains that not every job can be remote, but in the context where remote is possible, then leaders were probably already doing remote and hybrid work previously. Leaders were not sitting at a desk very often, they were traveling to conferences, visiting customer sites, other divisions, etc. You were already leading remote teams, but just psychologically tied to a desk. Acknowledging that the location of that desk is liberating, it is actually much less stressful for leaders. You can ask a question on Slack while at the conference, or take a call. It doesn’t have to wait until you’re back at the desk. It’s less stressful and increases productivity, and this allows top performers to rise to the top when you’re not looking at vanity metrics like how much time someone spends at the office.
  • 16:45 David remarks the importance of this observation about top performers and remote work. He asks Chris about the most common obstacles that he sees with his clients. Chris notes that in big companies, there is often a complete disagreement about if they are going to do remote or hybrid work. Chris talks about executives who stubbornly say that remote work does not work, even after seeing data of customer and employee satisfaction. This can be simply that it doesn’t work for that executive on a personal level, and so he tries to work with them on how to learn the new way to manage remotely. Older fashioned leaders will be resistant to this change. It’s no longer about “if I can see you, I can manage you.”
  • 19:36 In small companies, Chris sees a different obstacle: the senior leadership and owners don’t want to give up control. They say they want to grow, but they are reluctant to give out authority and budget that is necessary. Leaders of small companies often unintentionally designed the company so that everything goes through them. In order to cross 25 people, those owners and leaders have to get over that friction point and delegate.
  • 20:50 David talks about a client that he and Arin had, who surprised David by claiming that they had not worked remotely before, when in reality many of their employees already worked from home. For those executives, they saw remote work as meaning contractors in another country, and David had to coach them to understand that international contractors are no different than a local employee who works remotely from home.
  • 22:30 David asks Chris to define leadership. What do you see as leadership, and how it changes with remote work? Chris notes that culture is how we get things done – can you just go do it, or do you need 9 levels of approval? Is the culture high trust or low trust? Teams often have a subculture also, and how a team member feels about their boss, is also probably how you feel about the CEO and the company overall. To be a good leader in a remote environment, it comes down to what you focus on. What you focus on, grows. If you focus on trust, you’ll build trust in your team. Focus on the outcomes, but then let your team go do it.
  • 25:55 Good leadership is about creating an environment where someone can do a good job, and also where the leader is a mentor to their lowest and highest performers. People in the middle generally just want you to get the F out of the way. Middle performers are often not really interested in getting promoted and don’t need mentorship, they just need to be able to do their job. High performers are looking for the next step, and you need to mentor them in that. And you need to mentor the lower performers, so you can see if they have the potential to become a middle performer, or if they should just leave the company. Most leaders though mistakenly spend their time coaching people in the middle. The best leaders spend their time on the extremes of the team, and are good listeners when meeting with their teams.
  • 28:05 David agrees and says that the way he and Arin finally were able to grow was when they made the decision to hire the most self-disciplined and ambitious people possible. That allowed them to have a higher trust environment and focus on getting the work done. Chris talks about how his co-author Kim Shepherd had a recruiting company that was very cutthroat, and that worked for her, but would not work for Chris. You have to know the cultures you work best in, there is not a single solution for everyone. Business owners have to really decide what type of culture they want, and hire with that in mind.
  • 32:00 How do you determine if a job candidate has the right experience or diligence to work well remotely? Chris talks about a couple things that worked for him. Chris would send candidates a list of instructions for what they needed to do to get a personality test done, to schedule time on his calendar, etc. This was the first test, just to see if they could follow a set of instructions well. It was surprising how many people did not follow the instructions. His second filter is that he would send them the results of their personality test, as well as Chris’s own personality test or others they would work for. Chris felt this was fair to share the personality information in both directions, and he would look for a candidate to comment on what they found in the personality test. If they took the time to read his results and think about it, that was a big point in their favor. Finally, Chris had a fun question where they would ask people to explain the difference between Louis Armstrong, Lance Armstrong, and Neil Armstrong. Chris did not care how they got the answer, but how they answered told him a lot about their personality. For a sales person, he’s looking for them to be concise and engaging. For an accounting person to just give very short blunt descriptions seemed appropriate. If he was hiring someone for a research position, then he expected a more comprehensive answer. If an applicant got the answer wrong, that also told him something negative about them – they didn’t even try to google the correct answer!
  • 36:57 David asks what personality test they use, and Chris says they used the DISC assessment. Tony Robbins used to give a small version of it away for free on his site, but doesn’t anymore. Chris is also a big fan of the Strength Finders assessments. Chris had everyone in the company do a Strengths Finders assessments, and they mapped out the top 5 strengths across the company. This helped them realize they had a lot of people with the same personality traits, but very few people with other types of strengths. That helped them realize they needed to hire differently, and so Chris set a rule that they company could not hire anyone unless they had at least one of the Top 5 Missing Strengths in the company map. That led to increased diversity in their hiring in every way. It helped them with DEI goals, without specifying that anyone had to be hired with a particular background. It happened naturally based on looking for those missing strengths.
  • 40:25 If you’re recruiting someone specifically to work as a remote team lead, do you do anything differently? Chris says that a remote leader has to be someone who does not need credit for everything, they need to be a servant leader. Some of his best leaders have been introverts, they were not big talkers, but they did work well with the staff and listen well to them. They will be happy that someone else got a promotion in the team, and won’t take things personally. Chris could be the leader who pointed where to go, but he needed his lieutenants to be a softer type who can mentor and be good servant leaders to their teams. Chris wants people who are very rigid about the big stuff, and very flexible about the little stuff. Bad leaders are the opposite of that.
  • 44:35 Arin brings up a part of the book he really liked, where Chris talked about the types of remote meetings and had some creative descriptions for them. Arin asks, What are Cockroach and Tiger meetings? Chris pointed out they had to redesign their meetings when they went remote. One type of meeting they needed was an impromptu problem-solving meeting to get unstuck on something holding them back, and Kim and Chris named this the Cockroach meeting, which is always 15 minutes or less and optional to attend. Tiger team meetings are the opposite. Tiger problems are much bigger problems, and are usually a meeting called by a manager. These are mandatory, set roles, have an agenda, and may even be day long to solve a tougher problem. There are other types of meetings described in the book as well.
  • 51:30 You can learn more about Chris’s work at, including a list of his books available online.

Links from Episode 17 – Chris Dyer on Remote Leadership