Melissa Tan

I actually pulled them aside and I said, 'Hey, we need to move a lot faster. This is where we need to get to by X. We're a growth team. We need to prove wins out early.' And they don't have to be right, but just getting something out there, starting to line the whole team on what those are and then defining how we're going to measure success.

I actually pulled them aside and I said, 'Hey, we need to move a lot faster. This is where we need to get to by X. We're a growth team. We need to prove wins out early.' And they don't have to be right, but just getting something out there, starting to line the whole team on what those are and then defining how we're going to measure success.

I think the first time we started growth, we could have been more user-centric and been a lot more hypothesis driven. We were following a lot of best practices that just didn't really apply to Dropbox.

My aha moment of the value of first principles thinking was when I was at Dropbox. We would hire a ton of really smart people that had never done sales and had them do sales. If you take people that are just super smart, they've never done it before, one advantage of that is they can innovate because I think they come in with, I don't know anything. Let me just figure this out.

The more expertise someone has, the more it actually can lead to a false precision and then thinking they know what they're going to do. I actually think the expertise is more important later.

In that conversation what's important is also saying, 'I believe you can do all these things and I'm doing this to support you.' Or, 'I'm sharing this feedback because I believe in you.' Also saying that I'm here as support, as you are building that out, let me know what I can do to support you.

Even when I didn't have that role or responsibility or that scope, I sat there and I still imagined what I would do if I was in their position. And I think that's powerful. Pretend you're the CPO. Would you do something different? What would you do?

One of the biggest issues I see in organizations is when executives all have different goals, and they're not aligned on the same goals for the company. So it's like, sales teams over here are like, no, our goal is new logos. And you're like, cool, but in what markets, and how is that prioritized against what we're building from our product roadmap, and why is this not in sync?

If your executives and your board are telling you, I don't really know what's going on in tech or product. I have no idea if we're achieving our goals. If your executives don't know what you're doing, that's a big problem. So that's usually the sign, to me, that we need that.

I would try to ladder that up myself into a strategy and see if it was connected. And if it wasn't connected, that's telling me somebody's not formulating the strategy and deploying it down.

A good test is you go to all of your teams, and you ask them what they're doing and why, exactly what I was talking about before. And they all tell a similar story. We're working on X, Y, and Z because it goes into this initiative, and it causes this type of value for these customers, which, in return, is going to get us this business value.

I've met a lot of organizations that think most of their issues are in the training of their people. And 99% of the time I see that it's actually in the way that they're setting their goals and deploying their strategy. Because once you train those people, they have no context on what to work towards.

Really, strategy always comes down to asking the questions about how can we win, how can we get further to the goal, which is the vision. But it's also keeping into context of where we are now and what we're able to execute on now.

We take all the information we can, we make the best possible guess to go in one direction, and then we just keep reevaluating it to make sure it's the right direction. And if it's not, we pivot.

A lot of times, we just don't go and talk to other departments. And they have a wealth of knowledge. And we've got subject matter experts sitting in certain places that can fill you in on how the market's moving, and what things are happening there, and how people are innovating.