At the session for Building Your Dream Team at the Arizona Center for Innovation, there were two great mentors present to discuss ideas and answer questions from the incubator clients. The mentors are in leadership roles in tech companies in Tucson with many years of experience to share. They were great to have at the session.

At some point in the discussion, there was some sort of disagreement over an idea or a technical business issue between the mentors. I have no memory on what it was about now, but, at the moment it seemed like a pretty big deal as neither would let it go. I think at some point they agreed to disagree. It got pretty tense for a few moments though!

Now, don’t assume you know where I am going with this. You might be surprised!

Yes, it was a couple of tense moments and I got a little uncomfortable, wondering if the two were going to start full out yelling at each other (and what would we all do then? hide?). But if it was YOUR boss up there, and s/he HAD just let the point drop, what would you think of her/him? I think a teeny bit less, because it would show that they weren’t up on the latest information.

The only way out of the discussion was for one person to agree to disagree. And to be honest, I don’t recall which mentor first agreed to disagree. But if one had conceded the point, I definitely would have remembered that.

I believe that is the kind of personality that you need to have in a place of authority. A little bit stubborn. Given, you have to be well informed and a critical thinker to support your stubbornness. But someone willing to speak up and drive at making a good point is key in a leadership role.

How many times in your life do you look back on a team situation gone wrong and you think, if only XYZ person had listened to “my amazing advice”, the crisis would have been averted? Well, it was your fault that you didn’t yell loud enough and make a good enough argument for your advice to be heard! You were probably right, but you weren’t effective.  I think that is why a leader should have this “bossiness” trait. It is darn useful.

I think anyone who starts a company comes across this issue at some point: when to choose to be a pain in the patoot. With iTipArtists, Mary and I struggled to put together legal agreements. We didn’t know how to start. We met with mentors and lawyers but even after doing that we found we needed to understand what how to create an agreement on a truly fundamental level; we needed to hack through the painful process together for at least a few days. But it seemed that there was always something more important, more pressing to do when the two of us had precious time to meet. I tried to bring up the issue a number of times, but I didn’t do so effectively. If I had, we would have completed the agreements. I should have pressed the issue, even if a tad socially uncomfortable for both of us. We would have come out better for it.

Maybe it all comes down to confidence in being right. I know we all have our comfort zones about speaking up, but I am deciding right now if there is a 90% to 100% chance I am right about something, I will speak up in the future, and be stubborn about it. I think this is also good motivation to keeping up on reading and listening well to others; to make sure I have that 10% “margin of being right” in sight most of the time.