What does the finish line look like?

Good leaders paint a vision of the future that their team can attach to. As Adam Grant puts it in Originals, they create a gap between how things exist now and what they could look like:

The greatest communicators of all time…start by establishing “What is…here’s the status quo.” Then, they compare that to what could be making that gap as big as possible.

As inspiring as these alternate futures can be, they’re also typically a few years in the future with many miles between here and there. Your role as a leader within an organization is to motivate your team and set up a framework wherein that dream future becomes a reality.

There are (at least) two tricky aspects:

  1. How do you maintain motivation as a team when the finish line seems so far away (and often seemingly moving farther away each day)?
  2. How do you keep the finish line in focus when it’s months/years down the road?

The first piece can manifest in various ways. Teams can lose motivation in the middle of the journey or mistake a step in the right direction as crossing the finish line. It’s important to celebrate overcoming hurdles and making progress along the way, but it’s equally important to reinforce that these intermediate steps are just that, steps along the way.

The second piece becomes more evident as team members do the daily work required for forward progress. It’s easy to “lose sight of the forest for the trees” as the saying goes.

Grant provided two workarounds to help a team stay attached to the larger picture even as they’re heads down doing the actual work.

First, it’s so very important to reinforce that gap between the way things currently are and the way things could be in the future. We systematically undercommunicate this vision because it’s so familiar to us already:

You know the lyrics and the melody of your idea by heart. By that point, it’s no longer possible to imagine what it sounds like to an audience that’s listening to it for the first time. This explains why we undercommunicate our ideas. They’re already so familiar to us that we underestimate how much exposure an audience needs to comprehend and buy into them.

Second, invite others to help share your vision, particularly customers. They’ll offer a unique perspective and connect team members with individuals actually benefiting from their work.

People are inspired to achieve the highest performance when leaders describe a vision and then allow customers to bring it to life with a personal story. The leader’s message provides an overarching vision to start the car, and the personal story steps on the accelerator.

This piece about inviting customers to bring to life the vision with a personal story resonated in particular. Meeting real WordPress users at WordCamps around the country helps to reinvigorate the work I do at Automattic. Finding ways to bring in real-life customer stories into our work is something I’m actively thinking about.

What You Say vs. What They Hear

Communication is super important within any organization, but it’s particularly vital in remote work. At Automattic, we use the phrase “Communication is oxygen.”

The take-home message—building something amazing is impossible if everyone isn’t on the same page.

Any communication is better than silence, but aspects like clarity, actionable next steps, and an understanding of how everything “fits” can take a message from mediocre to “Hell yeah…let’s do this!”

A few weeks back, I was able to catch dinner with my buddy Chuck, and we were chatting about leadership and communication. I mentioned one communication error in particular that I was trying to address—reconciling what you’re saying with what “they” are hearing. This harmony is imperative for great communication, but I/we so often walk away from a conversation thinking “Oh yeah, made that totally clear” only to revisit the same idea two weeks later and find out we’re on different pages.

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