[CEO Friday] (Not So?) Terrible Advice for “Managing From Below”

David Barrett —  November 29, 2013 — Leave a comment

masterapprenticeI gave a talk this week at DreamForce called “The Entrepreneurial Instinct” (they picked the title) largely about the importance of trusting yourself and doing your own thing, and expanding on the ideas in this TechCrunch guest post.  One of the attendees wrote me with this question:

One thing I wanted to ask you was if I work in a company where I am not a senior level exec, capable of making the decision to experiment on ways to get our product to rapid adoption, how do I go about convincing them to just try something out?

Here’s how I responded: 

It’s a tough challenge, “managing from below”. I’ve used a variety of techniques when in that position, none of which are great:

– Just do it. Better to beg forgiveness than ask permission. However, this only works in areas over which you have total control and require no outside support.

– Selective obedience. Become a ratchet: stand your ground while waiting for someone to say something that can be interpreted as support for your position, and then use that as justification to move forward. Even if a compass is giving random directions, you can “follow it” anywhere you want by only giving it attention when it’s pointing the way you want to go.

– Creative misinterpretation. Most people are poor communicators and thus hold unstated assumptions, make ambiguous assertions, and generally fail to present a cogent argument. This gives you a lot of “wiggle room” — find a way to repackage your idea in a way that matches the outlines of what others are presenting.

– Master/apprentice inversion. People in charge love to feel like they’re in charge, but hate actually doing work. Challenge them outright and they’ll crush you, no matter how good your idea is. So convince them your idea was THEIR idea. This works well in conjunction with selective obedience and creative misinterpretation.

But really, if you find yourself often turning to the above, you should be looking for a new job.  To be clear: everybody is irrational at times, and the above are really just techniques for remaining productive in the face of irrational opposition.  Even in the best environments, and with the best people, this scenario will come up more than you like.  But if you feel that it’s gotten to a level where you feel stuck in your career and can’t advance, best to start looking around.  Incidentally, did I mention we’re hiring?

Thanks for writing!

After sending this, I started thinking “Wow, that’s some really passive aggressive advice.  I wouldn’t want someone to use that advice against me.”  But on second thought, I realized: actually yes, I would.

Again, these are techniques for how to productively deal with irrational opposition in a way that minimizes conflict.  If you find yourself reaching for this tool in your toolbox, you’re already in a pretty bad place, and none of your options are good.  And clearly, you’ll always try (or should try) more overt and collaborative techniques first.  But if all else fails and you’re forced to decide between “giving up” and “fighting to the death” (both of which are bad), some of the techniques above might actually be the better compromise.

In my case, I hope you’d rarely find the need to use the above.  I believe myself to be a pretty good listener, open to new evidence, and generally foster a creative environment of empowerment.  But if there’s a scenario where all that falls down and I’m irrationally holding on to some idea, and you genuinely feel your idea is better: I want you to win.  Even if you need to use dirty tricks on me to make that happen.

Because at the end of the day, we hire great people with good intuitive judgement.  And whatever the issue is, odds are it affects you more than it affects me.  If I can’t convince to you to my side of the argument, you’re probably right.   And if my argument is so ambiguous and inconsistent that you can package your idea and make me think it’s mine — who am I to complain?  Nice job.

When you have a team full of smart, passionate people, total agreement on everything is never going to happen.  And as the team grows, me knowing, understanding, and personally approving of everything is just impossible.  Clearly, my job is to stay out of the details — and I think I’m reasonably good at that.  But if I fall off the wagon, and you find me foaming at the mouth over some detail that I don’t understand but irrationally care about, do what you need to do to win.

Either you’re right and eventually I’ll come around, or I’m right and you’ll do the same.  Either way, it’s better for you to move forward in a productive path than get blocked by my irrationality.  And I’d hope anybody else you might feel the need to employ the above dark tricks against feels the same way.

David Barrett


Founder of Expensify, destroyer of expense reports, and savior to frustrated employees worldwide.

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