How to Survive the Messy Middle


Creating something from nothing is an unpredictable journey. The first mile births a new idea into existence, and the final mile is all about letting go. We love talking about starts and finishes, even though the middle stretch is the most important and often the most ignored and misunderstood. In this INDUSTRY Interview, Mike Belsito talks about this “Messy Middle” with Scott Belsky. Scott literally wrote the book on the messy middle based on his experiences as an entrepreneur and product leader.

What is the messy middle?

Scott used frustration as a source of inspiration for his book The Messy Middle. His frustration was with the obsession over starts and finishes of products and businesses. He didn’t like how the volatility that happens in between gets briefly summarized in a pithy descriptions akin to “and then a miracle occurs”.

The volatility is the highs and lows that inevitably happen in any “bold journey”. The highs are where you realize that your everything is just jiving. The lows are the times you have to work with no end in sight and no rewards to keep you engaged.

You’re not your best during the highs. You start to attribute the things you did to the things that worked. You become driven by false pretenses.

You’re also not your best during the lows. You make decisions out of fear and you get hit with every other anxiety that comes up in the midst of building something with no end in sight.

Ultimately, you want to achieve what Scott calls the positive slope, which is when every low is a little less low and every high is a little higher. The way to get that positive slope is to be very optimistic about the future, but very pessimistic and paranoid about the present.

What do product people need to know about the messy middle?

When Scott decided to put a book together about the messy middle, he reflected back on his own experiences and discussions with several other entrepreneurs. He grouped the resulting observations into three themes:

  • endurance – how to manage and navigate through those lows.
  • optimization – how to optimize the things that are working in product team itself.
  • final mile – how to deal with the self sabotage that occurs towards the conclusion of a bold journey.

Scott focused on a couple of actions you can take as a product leader to help your team reach the positive slope.

Be the narrator of the journey for your team. Remind your team that they are making progress because when people feel like they are making progress, they’re more likely to make more progress.

Find ways to short circuit the reward system of your team so you can stay engaged on a incremental basis for a long pursuit. People are biologically tuned to need short term rewards to keep moving.

Both actions focus on the ultimate competitive advantage in the product world – keeping your team together long enough to figure things out.

Were there any surprises when exploring the messy middle?

Scott did come across some surprises as he explored the messy middle. He found that successful teams allowed for some fighting because that indicates that people care about the solution. If there’s no fighting, that may be a sign of apathy.

Of course you don’t want to fight until you reach consensus. It’s better to have a culture of disagree and commit rather than always trying to get to complete agreement.

One of the reasons those fights spring up is because someone is convinced that something should be done in a certain way based on their intuition. You’ll want to make room for that, even in this data driven world.

And finally Scott found that many product leaders found that it’s important to separate yourself from your work in order to make it through the chaos that happens right before launch.

What should teams keep in mind as they grow?

Scott identified a few things that teams should keep in mind as they get larger.

He suggested that the playbook is the perfect playbook until it’s the absolute wrong playbook. You have to know when it’s time to discard the playbook for how your team works together.

Scott stated that “discontinuity is the greatest effort towards continuity.” In order to continue to thrive and scale and grow you have to keep shaking things up. One way you can think of doing that is to AB test the way you work as a team, just as you AB test your product.

When you have a growing team you should also embrace resourcefulness as a muscle you build. Avoid the temptation to just throw more people at it, and instead build the resourcefulness to solve the problem before trying to hire.

How do you narrate the journey for your team and leadership?

Scott reflected that you may want to look to marketing to identify some tools you can use to drive yourself and your teams to take action and to prioritize differently in the workplace. Use a visual version of the business plan or a prototype of the state of the product in the distant future as a force of alignment. After all, a prototype is worth a thousand meetings.

You have to manage expectations of leaders as to the state of a project and whether it is an experiment or a test or something you’re doing with conviction. Set the expectation early that you are going to run a series of experiments, and some of them will not work, but that you’re working to make sure you get it right by the last experiment.

Your team has to set its own measures. Don’t let someone else define what success looks like for you and your team. Define it for yourself, get buy in beforehand and then remind people what you discussed.

Any takeaways from the Messy Middle for product people?

Scott shaded the middle section of the book to call out guidance specifically focused on product people.

A key point in that section is think differently about the first mile of your user’s experience with your product. Keep that front and center as you iterate through your product.

If you’d like to keep in touch with Scott, you can find him on Twitter @ScottBelsky.

Kent McDonald

Kent J McDonald writes about and practices software product management. He has IT and product development experience in a variety of industries including financial services, health insurance, nonprofit, and automotive. Kent currently practices his craft for a leading agriscience company and provides just in time resources for product owners and business analysts at and Product Collective. When not writing or product managing, Kent is his family’s #ubersherpa, listens to jazz and podcasts (but not necessarily podcasts about jazz), and collects national parks.