I’ve mentioned that being a generalist gives me a good vantage point to see similarities and differences across fields and thus to gather a lot of tools and skills to use. But equally important is knowing when to use which tool for which job — that’s based on understanding transition and recognizing where you are in it:

  • A product transitions through the phases of the product development process or software development lifecycle.
  • A project transitions through the project management phases.
  • An organization transitions through growth models, workforce, and management approaches. 

If you’ve got a deep enough tool kit, you can pick and choose what’s going to be most useful for the work at hand, rather than trying to use a cookie cutter approach.  What you need for working with an early-stage startup, for instance, will be very different from what you need in a more established organization — not just because the work is different, but also because the people are different. Personalities often self-select to different stages of project and company.

recent 99U article about using sprints very early in the product development process highlights a key reason for adjusting your approach based on the stage of development:

While you can spend longer building a perfect prototype, that isn’t the point of the sprint—it’s a learning process, not a manufacturing one. Knapp has found that teams can get 90 percent of a product’s user interface finished in a single day. And that timeframe is important. “After a day you are definitely willing to listen to what customers say about your product,” says Knapp. “But when your prototyping goes on longer than that, you become more and more attached to the idea.”

But sprints may not be a useful framework in a later stage in manufacturing, for instance, where root cause understanding is more critical than feature building. That kind of work may be more investigative and documentation-based, requiring different tools altogether.

Sometimes you need to be rigid and focus on diligence above all else, and sometimes you need to focus on individual autonomy, loosen the grip, and accommodate different working styles above all else. The key is knowing when to use which approach, and that really depends on where you are in the interplay of transitions.

Here’s a short deck I made to illustrate the interplay of these stages, and what tools come to bear. Click on the arrows or on the slide itself to advance the deck.

No matter what tools you use, or what approach you take, you’ll only be effective if you keep empathy at the core. Managing transition is managing change. Transition is hard and  can be emotional, but you can make it less painful by setting expectations, clarifying process, and making sure everyone understands how to hold each other accountable to the process — all of which are driven by empathy.



Change management

There are a lot of approaches to change management, but for me, one of the most important aspects is transparency. Folks are never going to buy in if they don’t understand a) what’s happening, b) why it’s happening, and c) their role in the change.

This table does a great job highlighting all the ways change management can go wrong, and the emotion that comes with a poorly handled change attempt.


Successful change management is deeply tied to expectation setting, and facilitating the change throughout the organization, because change is emotional.

Psychologist Jonathan Haidt (The Happiness Hypothesis) introduced the metaphor of an elephant and rider to describe the interaction between a person’s emotional side and rational side.

The elephant (the emotional aspect) is much bigger and more powerful than the rider. If the elephant doesn’t want to go where the rider is telling him to go, you can’t make him. The rider is a planner, a think-of-all-the-possibilities-person, and if he doesn’t have a map and directions, he’ll lead the elephant in circles.

The Heath brothers (Switch: How to change things when change is hard) expanded that metaphor to include a third factor that they call the path, which is the environment, the situation. It’s about removing obstacles, and making it easier to go the right way. Portion control — there are studies that show folks will eat a whole container, whatever the size, so you can control the situation — the path — by making only smaller containers available. This is crucial because motivating the elephant — the emotional element of the brain — wants what it wants and will power is a finite resource.

Here’s a case study I did about implementing process improvements in a business process at work. Click the arrows or the slide itself to advance the deck.