I love the phrase Let's pretend. Let's pretend we're a B2B company. What does that look like? Who do we need to hire? What metrics will we track?’ It helps us explore new ideas without the fear of committing. It gives us the courage to innovate.

Let's Pretend Together

A lot of companies are great at executing against understood goals, but sometimes need help to get out of their comfort zone to expand into new products.

I design workshops that help executive teams navigate projects in spaces they haven't tackled before. One useful technique is helping them find their North Star; a "one-word" mission statement for a project or product.

"Once we have our North star, we can playfully explore the scenarios it leads us to."

We can pretend the product has launched and succeeded and we must reorganize the company. We can pretend it failed and explore pivoting.

Your North Star is emotional & inspiring. It should guide every choice you make.

You cannot pretend forever, not if you want to make an impact on a market. Planning is fun, but making is better.

Organize a Gameplan

I've seen companies struggle with making a decision-- I help make that a safe choice. As we explore scenarios, a favorite always emerges. "How could we test this choice using the smallest number of resources"?

The Lean Startup approach of hypothesis works well here. A scenario becomes a hypothesis, and then a roadmap becomes not a piece of science fiction but a series of experiments to discover the path forward.

Paul Saffo talks about the cone of uncertainty. The farther out you go from the present, the hardest it is to predict what will happen.

So we set up a roadmap for each quarter to focus on what will get our company on the right path now. This gets people excited about achieving together.

Finally, you must organize your people. Are you missing skills? Do you have people who will stand in the way of radical change? How do teams shift as plans change?

Execution is everything. A focussed team with a cadence of commitment and celebration helps make sure we're meeting the right goals by shipping the right products—together.


1. Assemble The Right Team

1 interaction designer + 1 visual designer + 5 engineers != Magic

Your teams often have to change, & building teams is really hard. Everybody wants an easy formula.

But people aren't cogs. If you build teams based on titles, you'll end up with duplicate skills or gaps in expertise. Who are your anchor people, the folks who can lead, and what skills do they have? Now how are you going to complement them?

I help organizations find the answers to these questions, and build their teams for success.

2. Measure The F%#@ Out of Everything

Objectives and Key Results (OKRs)

I'm the the person that gets things done. And I really like OKRs because they are really good at getting things done.

First you set a time-bound qualitative goal— that's your objective. It can be as messy as “be the awesomest new search startup in silicon valley”, or "successfully launch a social feature". Then the Key Results define that messy objective. What is awesome? What is successful? Adoption, growth, virality, revenue? What can you do in a single quarter if everyone pulled together?

After I help people discover their predicaments and sort their ideas, OKRs help us get things done without distraction. There are a lot of tools, & OKRs are one of my favorites.

3. Create a Cadence of Commitment and Celebration

What does a Monday look like at your company?

Start the week by committing to push one step closer to your group's OKRs. It's not about the boss telling you what to do, it's about committing to each other; and that can move mountains.

I'm a big fan of Friday demos where every single person shows off the software they built, the designs they made, or announces sales or bizdev deals.

Everybody has to say “I moved the ball forward this much this week.”

It's a cadence of celebration, and has to be part of your team's life. We discover together, plan together, and execute together. We commit to each other, and celebrate as a team. Great teams do great things.

Every so often, a company has to do something incredibly hard, and incredibly important. They hire me to help them make impossible things happen, and I make it happen.