Tackling Risk Head On: Interview with Dan Milstein

Even on a shaky phone connection, engineer and entrepreneur Dan Milstein commands attention. He’s worked at several startups over the years, including HubSpot, and shows no sign of slowing down. If anything, this business-minded developer is hungry to take the lessons he’s learned from failed ventures and apply them to future endeavors. On the first blog post of his newly created software and product development consultancy, Hut 8 Labs, Milstein talks about the importance of running an effective post-mortem on startup failures.

According to Milstein, the most common human response to failure is shame, and no one wants to talk about why things went wrong. But not talking about failure can be detrimental to startups through missed opportunities to make valuable improvements but also to perpetuating damaging patterns in the team.

I caught up with Milstein recently to delve deeper into what causes failure and how teams can beneficially work with and address it.

For Milstein, failure can stem from anything as small as not getting a piece of work into the right hands soon enough to as large as a mismatch in identifying a common pain and the common solution to that problem. For our conversation, we focused on the larger conceptual failures in which the startup may not even know it has a problem:

“It can feel like you’re making progress when you’ve talked to a whole lot of people and explained, ‘Here’s how I think you feel,’ and [they] say, ‘Yes, that’s exactly how we feel.’ And that can feel really validating, but until you actually have something that they’re buying from you that solves that problem, you’re potentially pretty far away still.” 

Many startups make the early mistake of being able to correctly identify the problem in their market, but they may slip up in offering the solution. Milstein notes that “not everyone may want the same solution.” If you want to offer a solution that people will be willing to buy, everyone in the startup must be tasked with answering a common question: 

“We have this common pain. Our question is now, ‘Is there a product we can sell into that pain?’ That’s a sales question and that’s a product question and that’s an engineering question. Can we actually build something that we can sell that people want. If you get everyone involved to understand everything they’re doing is to answer that question, then all your product questions and all your engineering questions and all your sales questions should fit into that overarching goal.”

However, Milstein observes that startups often silo responsibilities: engineers are responsible for building the product, product managers for making decisions about what to build, and sales for getting people to buy the product. And this is a mistake. Teams, instead, need to unify around answering a common question.

Answering questions is about tackling risk head on. Milstein defines a startup as a “team of people who are trying to make a new product or new service in conditions of extreme uncertainty,” and this uncertainty can be paralyzing if you don’t address it. Siloing responsibility makes it harder for teams to address risk together. Startups need to “focus on the risks rather than pretend they aren’t there” and understand that “in conditions of extreme uncertainty, you’re going to get things really badly wrong”

In closing, Milstein offers the following advice to leaders for tackling uncertainty and risk with their team:

  • Leaders have to accept that they, themselves, don’t know the answers (in fact, they likely don’t even know the right questions)
  • They have to have the confidence to openly share that uncertainty with their team
  • They have to then celebrate when their team learns things, even if the things learned mean that the hopes / plans of the company are going to have to change
Post Link