Lessons From A Recovering “First Time CEO”

I got cornered at work the other day (socially distanced, of course) asking if I am still blogging. <Gulp> That’s not a good sign that I’ve been diligent about finding time to share the stuff on my mind lately?!? Thanks to both of my regular readers for the reminder to get back to writing (insert mental ass kick picture)……

I like spring the best. It is a time of personal renewal. The weather is nicer and I enjoy getting outside and exercising more. The golf courses open back up and I love being able to walk outside for a few hours with my own thoughts. Professionally, it is also “Annual Meeting Season” which is a great way to look back on past work and think boldly about the future.

This year, I found myself a little more reflective on my tenure as a recovering “First Time CEO”. There has been much change and turnover in CEO roles in our industry lately and it has caused me to reflect on my ten years being a CEO at Conexus. There are lots of lessons in my first experience as a Chief Executive. Here are a few lessons from a recovering “First Time CEO”, along with some “Rookie Tips” for you to think about when you are faced with a new, expanded role:

It’s Can Be Lonely

Once you become a CEO, you don’t really have a Team of “peers” any longer. The relationships are just different than they used to be when I was not the leader of the team but a member of the team. It takes a long time to get to the point where people are brutally honest with you about your ideas, your performance and your leadership. In fact, some might never be as honest with you as they are with their other colleagues. I have lots of examples in my tenure where a colleague finally shared some feedback that was hard for them to say. I wish so much that they would have had the courage to tell me in real time or as soon after as was practical. After a decade it gets better but keep in mind that over that time, you also add new members to the Team and lose members of the Team, so the journey to get to the point that they all share openly with you takes constant effort. The lack of direct feedback makes it a lonely place.  Rookie Tip: Find a network of peers (in my case, it was other CEO’s from my community and my industry) that you can connect with, learn from and commiserate with.  It won’t replace what you had as part of the Team, but it will help.

You Are Only Human. And Flawed. Just Like Everyone Else

As a first time CEO, I recall vividly being so afraid to make a mistake. All I could think about was 1,000 employees (in the case of Conexus) talking about how some “wet behind the ears” new CEO had just screwed up. The irony is that the sooner you recognize your own vulnerability and imperfections, the more likely people are to want to follow you. The easiest way to do that is to be honest about your mistakes and your own shortcomings as a leader. People want to work with and for other humans – warts, flaws and all. Last year, I wrote about our Fail Forward awards and our own learnings in recognizing the opportunities from failed innovations. Rookie Tip: The sooner you can model the honesty and transparency around failing and learning, the more acceptable it will be in the organization to try new things and not expect perfection. Your first broad public admission of failure to your work family will be very hard. But I promise, it gets easier. I speak from experience.

Working With And For A Board Is Very Different

I recall my first Board meeting like it was yesterday. It was October 21, 2011 – just four days after I started and I was scared stiff. I had been to lots of Board Meetings but never as a CEO responsible for the entire organization. Adding to my stress was the fact that we spent much time at that meeting talking about a failed project that had cost the organization a significant amount of money at the time. In my ten years working with a Board, there are few things to note. First, they are just real people trying hard to do good work and make a difference. They are not there to make your life hard or miserable, merely to oversee Management and to create healthy tension in the most significant decisions that organizations face. Rookie Tip: Embrace the healthy tension. Respect the role they hold and do your best to serve them as the representative of the owners. Ask permission before you share your opinion on decisions they own and solicit their candid feedback on the decisions you believe you own. Remember also that they are humans just like you (see above). When you work for a Board, there will be a number of opinions on pretty much everything you consider or propose. Not everyone around the Board table will always agree with the decisions that are made or how you implemented those decisions but you work for the Board as a collective not individual Board Members and it’s really important to learn the difference.

What You Do Matters Way More Than What You Say

When I talk about leadership now to younger, emerging leaders, I speak about the “backpack of leading”. Like everyone else, the Instagram stories of CEO’s do not reflect the totality of the work that is done. My day is not just engaging with community organizations, governments and watching Cultivator pitches. In my case, 1,000 people are watching my feet way more than they are watching my mouth. How I behave matters. For example, I can suggest on a video communication to the company that it is really important to create a coaching culture where development of our human talent is critical. If it is so critical, I better find the time (see below on time management and choices) to observationally coach, to mentor and to continue developing myself. If it matters enough for me to ask others in the organization to do it, it matters even more that I do it. Consistently. Rookie Tip: Don’t let your ‘little birdie inner voice” tell you that your leaders are more self sufficient and they don’t need coaching just because they have some fancy title. I started to do less coaching of my colleagues a couple of years ago and then ended up having to apologize for the error. If it is important for the organization, it’s equally important for people to see CEO’s lead by example. Imagine now when I show up unannounced to the Team Meetings of my direct reports and let them know I am just there to invest in my colleague and provide them some feedback. It becomes a powerful moment of reinforcement and my colleagues regularly tell me how much the investment of time means to them and their development.

You Will Get More Credit And More Criticism Than You Deserve. Share the Credit and Wear the Criticism

Are you a sports fan? Have you heard the analogy that football quarterbacks get too much credit when the team is winning and too much criticism when the team is not? Being a CEO is much the same. When the organization produces great results or a winning idea, people generally want to give the CEO credit. Conversely, when things don’t go so well, CEO’s get much of the blame. The best CEO’s I have learned from figured out how to ensure that the credit gets spread around to those that worked so hard to create that result. Conversely, they also stepped up and took much of the blame when the organization was not able to succeed for whatever reason.  Rookie Tip: Find ways to spread the love and also to shoulder the criticism when necessary to allow the organization to learn, grow and succeed from the setback. It might not be fair but it is part of the deal.

You Will Be Expected To Know Everything And Guess What…You Don’t Know Shit 🙂 

When you get the opportunity to lead new areas of the business, the natural reaction from new leaders is to try to convince those working in that area that whomever hired you, made a good choice. You want to show them that you are technically brilliant in their area of responsibility. Guess what – as a first time CEO, you don’t know shit. Looking back to my own experience having grown up in the operations side of the business, I had never led (i) a human resources department, (ii) a risk department or (iii) a finance department. I remember vividly my first Executive meeting at Conexus, having started the meeting talking about what my background was and where I thought I could add value – operations, strategy, leadership and innovation. Then I quickly acknowledged openly the areas of the business that I had not led before and how much help I was going to need from the team in those areas. My new colleagues shared how they appreciated the transparency and at the same time, how they would work hard to help me learn other parts of the business. Rookie Tip: I had a great mentor at the time and I remember him telling me not to pretend to be an expert in all areas of the business. He told me that they already know there are areas I likely am not an expert in and trying to convince them makes little sense. He was so right. The early admission helped me set myself up to learn quickly as opposed to trying to portray a level of competence that did not exist.

Make Great Choices With Your Time (Wellness, Hobbies, Thinking Time)

When I first moved to Conexus, I immersed myself in the business. My family did not relocate for some time after I took on the job and I used the extra alone time to read, learn and meet our team and our communities. The first few months were gruelling. The problem with that was that it was not sustainable and it really didn’t model what high performing executives do to be successful. I forgot the other things I needed to do in order to be a consistent, healthy, high performing leader. Therefore, I didn’t eat well, sleep well or exercise nearly enough. I also did not spend nearly enough time thinking about strategy and really owning the part of my role as Chief Strategy Officer. Eventually, I had forgotten how to incorporate those things into my routines. It took me a while over the first few years to regain those habits. Rookie Tip: Go into any new role protecting fiercely the things you need to do for yourself to be at your best. Know them, practice them and make them known to those around you so that you can get feedback when you slip.

Your Job Is Not To Finish, But To Leave It Better Than You Found It

Transforming organizations is never done. It becomes a very hard mental game when there are always new challenges to respond to, new opportunities to seize and a constantly changing environment to do it within. As an emerging leader, you sometimes get opportunities to put a bow on some work and call it complete or paint it done as Brene Brown would say. As a CEO, you will never get an opportunity to finish the job. Rather, you have to accept that your success will be measured by whether you left the organization in a better place than when you were hired. Rookie Tip: Make yourself slow down from time to time to recognize the progress that the organization is or has made. It is a bit like watching your kids grow up. Some days you wonder if they are learning new skills or growing into the adults you want them to be. Then, when you look back at pictures of them from a few years earlier, you quickly realize how different they are and what substantial progress they have made. As a CEO, force yourself to look back at the “pictures” of the organization from years past and realize the progress the organization has made. You will never be “done” but this progress will fuel you to keep going.


Ten years after joining Conexus, I think about my first few days as a CEO from October 2011 often. I look back and wonder how I ever survived the early years of finding my way and learning how to be a better CEO. I should probably thank the Board of Conexus from back in those early years for giving me a chance when I clearly had much to learn. I am still on the journey to become a better leader and a better CEO and like the organization, I will never be done.

Taking time like this to reflect on the last ten years reminds me of all of the lessons and also motivates me to continue learning and growing — right along side of the organization. What have you learned on your leadership journey that you wish you would have known earlier? Drop a comment in below so that we can all learn together.


12 replies
  1. Glen Dyrda
    Glen Dyrda says:

    Thanks for sharing your perspective on this Eric. I found your comments on the interrelationships between CEOs and the Board very interesting, and there were a couple of nuggets there for me. I have never been a CEO, but I have led large teams and have coached CEO’s. Although it is really tough to do in larger organizations, one of the most important things I tried to do was to get to know all my team members as people (how many kids, what are they up to, what interests do you have etc.) and then make a mental note of those things and ask about them the next chance we had to interact, which might be weeks later. it goes a long away when you ask whether your son made that hockey team he was trying out for. Of course it has to be sincere, not contrived, but people will follow you over that wall if they know you are human, like them, as you have pointed out, and are genuinely interested in them as humans not just co-workers. Best lesson I ever got from someone I worked with (unfortunately, he was the opposite of that, and an ineffective CEO as a consequence). Great article!

    • Eric Dillon
      Eric Dillon says:

      Love this Glen, how does that saying go – people don’t care what you know until they know that you care. So true. I have also had the same experience you had earlier in my career and watching ineffective leaders can also be as great a source of wisdom as watching those who do it well

  2. Monique Goffinet Miller
    Monique Goffinet Miller says:

    Thank you for this honest depiction of a CEO’s reality. I love reading your blog and always learn so much.

  3. Tom Dutta
    Tom Dutta says:

    I became a CEO at age 31 and still to this day I say “I didn’t know what it was” This article reminded me of that time in my life. I had just remarried, had a child on the way and stepped into something that was equivalent to a turnaround.

    If it wasn’t for joining a peer community and putting my ego aside to finally acknowledge I didn’t know sh*t 🙂 I wouldn’t be the leader I have become today. The article is well done I don’t have much more to add except these final thoughts.

    I was given a book in my rookie CEO year and it was never lost on me the following passage…”When the CEO sneezes the office catches cold”. When I get up in the morning I realize I own the culture of the company and that is why the top job in any company is so difficult. Life isn’t easy yet CEO’s have to show up consistently no matter what goes on in and outside the office. I realized that managing business, family and my self were equally important. Thanks Eric for the article.

    • Eric Dillon
      Eric Dillon says:

      Well said Tom. Not many get the chance to be a CEO at 31! You are so right about having a disproportionate influence on culture. Appreciate you stopping by for a read. Hope you are safe and well and enjoying life!

  4. Tarique Khan
    Tarique Khan says:

    Eric, a common theme that I notice following your blog and various interviews/podcast is the fact that you always want to grow, learn, and that your biggest fear is not being able to keep pace with change.

    It made me rethink how I perceive myself. I like to think that I know it all, especially when it comes to my job, that my learning days are behind me. Seeing a CEO at your level who wants to continue to grow and learn has made me realize a harsh truth that I need to change my perspective.

    Thanks, man.

    (BTW, I posted this comment on Linkeidn as well, but I wanted to make sure you saw it, since some things you talk about made me rethink things). .

    • Eric Dillon
      Eric Dillon says:

      Thanks Tarique for sharing. We talk at Conexus that organizations don’t change, rather people do. That will therefore require everyone in the organization (CEO’s included) to build new skills and add value in new ways in order to meet the strategic needs of our members.

  5. Peter McCann
    Peter McCann says:

    Superb comments and valuable contributions to the insights of aspiring, new and seasoned CEOs.

    Some of the lessons are lessons that I have learned the hard way, and learning from our mistakes is better than not learning, but the best of all is learning from others – and Eric Dillon’s comments are a fine start. Thank you.

    I have already forwarded this link to a few people who will be interested.

  6. Richard Corder
    Richard Corder says:

    Thank you so much for sharing your authentic self Eric! I love the candor and humility that you share in your words – and am reminded that words make worlds. The one you are creating for yourself and those around you is bright, appreciate you! Thank you!

  7. Morris Smysnuik
    Morris Smysnuik says:

    Hi Eric — awesome piece. Looks like the beginning of a book to be written!!! This is the kind of advice that would certainly give a new CEO a significant leg up in beginning her/his career. Take care, and stay safe.


Leave a Reply

Want to join the discussion?
Feel free to contribute!

Leave a Reply

Your email address will not be published. Required fields are marked *