The CEO’s Challenge:
Engineering Alignment

Recently, my co-founder and I shared a simple but profound story with one another: our perspective of how Chewse began.

We chose our beginning and talked about what scared, delighted, and excited us. Not the facts that you share with investors or the press —we indulged in the feelings and perspectives that rarely get communicated.

As we re-told our story, it became clear that there was a strong theme to how Jeff and I had weathered the storm of building a company.

We are not:

  • the most qualified (this is my first job out of college)
  • the most experienced (we’re first-time founders)
  • the most supported (the road to finding our investors and advisors was long and difficult)

We are:

  • tenacious
  • passionate about our space
  • aligned at every major turn in the story

That’s when I had a realization, 4 years after starting the business:

My 1 job as CEO is to achieve alignment

Throughout our journey, Jeff and I have always come together to ensure we want the same things and want to travel the same path to get there. I see the CEO’s job as the Railway Engineer. If the tracks aren’t perfectly aligned, then the train is going to run in starts and fits — and you’ll never move with speed. Even if hammering the tracks into place delays the send off of the train, it’s worth it. Build thoughtfully to move quickly.

Some techniques I use to align my team:

  • Start meetings with the “WWW” — If I initiated the meeting, I answer the question, “What do We Want out of this meeting?” Do I want to figure out the next 12 months of sales quota structure or just focus on getting July figured out?
    This technique ensures that my teammate and I can come to mutual agreement on what we want from our time together. We sometimes spend 5–10 minutes upfront simply hammering the tracks into place. But it makes the rest of the meeting go more smoothly, and it feels SO satisfying to achieve the WWW.
    I also add a “Bonus” section if we achieve WWW and have time to go a bit farther than expected. Who doesn’t love a bonus round? :)
  • During conversations, I tell people what I’ve heard — I can’t tell you how many meetings I’ve left thinking I heard what the person was saying, and realizing they were trying to say something else entirely. What is said versus what is heard are two different concepts.
    To ensure I’m hearing what people are saying, I like to recap big points with, “This is what I heard based on what you said” or “What I’m hearing is…” People can then jump in and correct me if they don’t feel heard, or they tell me I’m on the right track. Then you have a choice on whether or not you agree and how you move forward.
    PS — This is also a great tactic for reference checks on candidates, since it ensures you are hearing what the reference is saying instead of submitting to confirmation bias of what you want to hear.
  • After big, meaty conversations, I send an email recap — Sometimes I leave a meeting saying something and realizing I was never heard. For my weekly strategy meeting, I send a brief email recap to my management team. In it, I bullet point the conclusions we came to in our discussions (if you haven’t noticed, I’m a big fan of bullet points). This gives people another opportunity to hear me and ensure that they were heard as well.

I’ve struggled with how much energy I put into this alignment piece instead of the execution piece. I now feel strongly that it’s worth it.

What else are you doing to create alignment in your daily work? I’d love to hear it!