Andy MacMillan | Crain's Portland

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Andy MacMillan


Act-On Software develops cloud-based marketing automation for small- and mid-sized businesses.

The Mistake:

Early in my product management career I was an executive at Oracle and had a fairly large development team. I had just taken over a new product line. To build credibility with the engineering team, I wanted to learn about the actual technology. So I went on Amazon, and I bought a book about writing code through this product, and I started teaching myself — a former programmer — how to write some code for this product.

During a one-on-one with one of my direct reports, I asked him at the very end about something that wasn’t working for me with the product. I didn’t explain why I was asking. I just asked him a question. What I didn’t realize was that he took that as, there is a problem with the product, and it got escalated to Andy. Not that I probably wrote some bad code on my own.

I found out a day and a half later, when he called me, that they had built an entire mini-war room in the engineering center and brought in all of this hardware and pulled the engineering team off what they were working on to try to resolve this fake issue I had accidentally created with my own bad code.

I was trying to get to know this team and build credibility, and I had to own up and say: “Hey, this is probably just an error in my code. I don’t actually know what I’m doing, and there is no customer issue here. None of you should be working on this right now. Go back to building products, which is what all of you do for a living, and I’m supposed to be helping you do that.”

The transparency helped, and they all got a good laugh out of it once they were over their initial shock that this big issue wasn’t really an issue at any level. But it was a very interesting moment for me in thinking about, as a leader, communicating not only the what but also the why and even the importance. Being able to tell my team: “I’m thinking about something. Let's all talk about it, but don’t send the troops out to go do this.” And then being really specific about stating, “Okay, now let’s go execute this. This is something I want the team to do, not just something I’m batting around as an idea.”

I had the ability to get a whole bunch of people to do a whole lot of work in five minutes and 10 sentences.

The Lesson:

As a leader communicating an idea or a thought or something that I’m working on, I try to be clear. Is this something I want the team to go work on? As a product person, especially in tech, we have a tendency to get excited about things. A shiny object goes by, and we all get excited. You need to be explicit. Is this an interesting conversation in a management meeting about something we might go do? Or is it something that we are telling people to go do? Those are very different conversations.

Sometimes we have a tendency on our teams to say: “My boss was interested in this idea. Why don’t I go find out a lot more about it and get the team working on it?” And sometimes interested just means I read an article about it 10 minutes ago. I wouldn’t want (anyone) to go burn a bunch of effort on it. It’s just a topic.

When we talk about companies that suffer from "strategy of the week," I sometimes wonder if it goes back to this kind of stuff. They are not trying to change the strategy of the company every week. It’s just that interesting things are going on in the market, and there are concepts that the team could be pursuing. We have to be explicit about which ones we are doing, and which ones we are talking about but are not going to pursue.

I had the ability to get a whole bunch of people to do a whole lot of work in five minutes and 10 sentences that I inadvertently said in a meeting. So now I’m very deliberate when I talk about a problem or an issue or an opportunity, if I’m serious about going and doing it, or if it’s just that we’re kind of pulling a thread a little bit as a management team to see if it might be interesting.

Follow Andy MacMillan on Twitter at @apmacmillan

Pictured: Andy MacMillan | Photo courtesy of Act-On Software

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