7 Unexpected Takeaways from My Curbside Conversation With a Company Leader

Photo by Quest Technology Group

As I wrapped up my laps around the neighborhood Saturday, I stopped to catch up with my across the street neighbor Steve. After 20 years, our typical conversations revolve around the infrequent home sales, lawn service companies, and messy oak trees that refuse to hang onto their leaves.

But this conversation was different.

Steve has a C-level seat with a national company that is rapidly expanding through acquisitions. Frustration with their technology team and concerns about their Frankenstein infrastructure were weighing heavily on him.

As I listened to Steve, it was clear he was looking for an objective sanity check.

o Are we behind because we’ve just implemented x? (embarrassment)

o Shouldn’t our IT people be able to answer these questions? (frustration)

o Are my concerns realistic? (reassurance)

o How do we get our hands around an ad hoc collection of applications? (strategy)

o How do I help the rest of the C-team to get past overwhelm? (leadership)

Humble Words

It was so tempting for me to ask a lot of questions that would have taken us down too many distracting black holes. What was more important was my giving him the room to vent and dump his thoughts. Technologies, tools, and skills would come later.

What he said several times was “We don’t know what we don’t know”. That’s a very hard thing for most of us to say out loud, and yet it’s one of the most transformative steps for learning and practical problem-solving.

Think Like an Algebra Word Problem

As we wrapped up the conversation, I offered our help, starting with this single focused exercise — create a where-are-they-now visual.

They have a cobbled-together collection of applications, many of which were hastily purchased for one person. He was wisely concerned about the integrity of these applications, who had access to the data, how often they were updated, the list went on — and on.

This clear picture of their application framework combined with a thorough network discovery would become the roadmap for their technology infrastructure decision-making.

But for now, just draw the blueprint.

Don’t worry about what’s next.

It was his reaction to that last sentence that was completely unexpected. When Steve heard that he didn’t have to think about what to do next, he visibly exhaled and relaxed. Shoulders came down. It was a thing of beauty.

I didn’t see that coming at all.

We all promise ourselves that we’ll take one step at a time. But our non-stop, get-it-done-now brains aren’t on board. We continue to feed our overwhelm and add to the stressful to do list.

It’s time to stop this mental madness.

Remember those horrifying word problems we all suffered through in algebra class? When we learned to slow down and put each word into context, the problems became solvable — well, at least most of the time anyway

Why did I share this story with you?

Every once in a while we get lucky and have one of those conversation we wish we could have more often with clients.


1. We don’t know what we don’t know is a healthy balance of confidence and humility.

2. Encourage saying “we don’t know what we don’t know” in your organization. Everyone wins.

3. Approach problem-solving like an algebra word problem. One word at a time. Don’t get hung up on the next word yet.

4. Practice asking, “Is this the right solution?” instead of firmly stating, “This is the right solution.”.

5. Be honest about the services you provide to your clients — and what you don’t. When we aren’t clear about the services we deliver, our clients are going to make assumptions. These fill-in-the-blanks stories lead to unnecessary frustration, unmet expectations, and lost relationships.

6. Make a list of 10 things you can share with a client that will reduce their anxiety level.

7. Make a list of 10 things you can do to simplify a big goal. Practice James Altucher’s idea subtraction (affiliate link).

One Final Thought

Thinking back over the conversation, I realized one thing I never heard Steve say was, “We’re doing it this way.” Period. End of discussion. Instead he asked, “We’re doing this. Is this the right thing to do?

As Dr. Seuss said, “Sometimes the questions are complicated and the answers are simple.”

That’s one of those complicated questions that leads to simple answers.

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I put technology to work to solve business problems and create unexpected opportunities. Endlessly curious. Avid learner. Word nerd.Site: https://bit.ly/2tl18Uu

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Linda Rolf

Linda Rolf

I put technology to work to solve business problems and create unexpected opportunities. Endlessly curious. Avid learner. Word nerd.Site: https://bit.ly/2tl18Uu

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