The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

by Scott Belsky

Break incrementalism by questioning core assumptions.

While so much of a great product comes down to your relentless efforts to simplify and refine, you’ll also have to make bold changes along the way.

By proactively integrating fresh talent and empowering its newest people to make the company’s mission personal, Meetup escaped incrementalism and made bold changes.

Old assumptions don’t get questioned enough because we’re used to them, and new ideas get dismissed too quickly because they are foreign and challenge conventions.

Recognizing an innovation is important. But what makes employees experiment and share their ideas in the first place? How do you ensure that the managers recognize and support a small tweak or inbred innovation that could make a big difference?

If you don’t support inbred innovation, your team’s indifference to the future of their own creation will halt its evolution.

Empathy and humility before passion.

Empathy for those suffering the problem must come before your passion for the solution.

Build your narrative before your product.

For Behance, our narrative was about the plight of creative professionals around the world whose careers were under siege and too much at the mercy of circumstance. Designers and illustrators and countless other creatives didn’t get proper credit for their work.

The leaders of thriving communities (online and off-) act as stewards, not owners.

If so much of the future of business depends on building networks, then we need to rethink the role of leaders in business.

PR is very helpful when a company needs to explain itself. Otherwise, it just gets in the way, especially for early-stage teams.

Identify and prioritize efforts with disproportionate impact.

Measure each feature by its own measure.

“In preparing for battle, I have always found that plans are useless, but planning is indispensable.” So said Dwight D. Eisenhower,

Like Tim, we should all make a few bold bets early in our career to do something first and redefine a category.

Our natural drive to say yes to as much as possible, if only for optionality, may help us in the beginning of our careers but hurts us later

Don’t optimize for the best deal now at the expense of long-term outcome.

Aggressive negotiations might get you more money in the initial paycheck, but they run the risk of setting a hostile and mistrusting tone for the relationship going forward.

When negotiating a deal, I’ve always aspired to be fair. It’s simple: I have a discussion up front with my counterpart in which I make the case that, philosophically, I am interested in an outcome that sets us up to succeed, and I therefore want to reach the fairest deal for both parties.

Don’t underestimate the criticality of timing.

Hiring managers tend to focus on the fit of a particular leader in a company without factoring in timing.

Companies have a unique set of needs and opportunities for different phases: Sometimes you need leaders who will drive product innovation, other times you need leaders who will masterfully sustain incremental growth.

Sometimes a product needs a “flag planter,” and sometimes it needs a “road builder,” as Shantanu Narayan, Adobe’s CEO, once put it.

In my experience, these leaders are rarely the same people. Like dating, a great match is as much about timing as it is about capabilities and shared values.

The ideal leader for a company changes as the company changes.

One of the most important lessons I have learned over the years, as a generally impatient person with idealistic tendencies, is to wait for a process to unfold.

Achieving a vision without breaking the system requires periods of generating buy-in, exhaustive testing, and allowing time to pass for ideas to sink in and the right people to get on board. It is frustrating but true that, in most cases, companies and products should change only in careful increments.

Pacing is very important. But sometimes your team and product are at an inflection, and a trigger must be ...

The leaders I admire most maintain healthy incrementalism while imposing the occasional transformat...

The inevitable outcome of any business governed by too much incrementalism is a limited market size because the local maximum—the one thing that has worked in the past t...

Sometimes you need to take a leap, not a step.

The best teams know when the time has come to make the bold move and can reorganize to pull it off.

Great leaders are generally even-keeled but able to make an unpopular decision at the right time, even when such decisions ...

The best teams I come across are parlaying forces already under way in their favor.

In almost all cases, best to ignore sunk costs.

At a deeper level, ignoring sunk costs is about allowing yourself to change your mind, despite whatever plans are in motion or how strongly you have already advocated for your previous opinion.

Jeff Bezos once remarked in an interview that he didn’t think consistency of thought was a particularly positive trait.

Bezos is known to encourage self-contradictions.

your default is to cling to your original convictions, you’re more likely to be wrong in a fast-changing environment.

The real reason we cling to our original convictions is the energy, time, reputation, and money we invested in them. These resources are sunk costs

You must also resist the impulse to make “halfway changes” that attempt to recover some sunk costs.

Great work is seldom the result of repurposing stuff that didn’t work.

Mine contradictory advice and doubt to develop your own intuition.

great advice in one context is horrible advice in another.

“Never follow your investor’s advice and you might fail. Always follow your investor’s advice and you’ll definitely fail.”

“Look for investors that respect the fact you’re not always going to follow their advice.”

The best advice doesn’t instruct—it provokes.

People love taking down something that is new and unfamiliar.