ISSUE #109

A simple way to pick what goes in your plan.

90 days is long enough to build a reputation in a new leadership role, and short enough to spend it on the wrong things.

Most new leaders don't fail at making a 90-day plan. They fail at choosing what goes in it. The list fills up fast: the dashboard the CEO mentioned in your first week, the tool your old team loved, the reorg that looked obvious from the interview, the quick fix that would make your first update look strong.

Every item on that list is defensible. That's the problem. When everything looks reasonable, new leaders tend to pick by speed and visibility, because those are the things they can see.

I've watched many leaders build their first quarter this way. The early updates look great. Then, around month six, the hard change they were hired to make arrives, and they discover they've got nothing to spend on it.

Early wins aren't there to prove you're busy. Everyone already assumes you're working. Early wins buy credibility, and credibility works like currency. You save it in the first 90 days and spend it later, on the changes that take six months to a year and genuinely upset people.

Seen that way, something uncomfortable follows. The easiest wins are usually the wrong ones. The easy win is the one you can finish alone. The right win is the one your bigger goal runs through.

When I started as CIO of a mobile development startup, seven of our clients were about to walk. The obvious first win was a big new logo. I went after the seven renewals instead. They were slower and far less impressive, and they needed sales, product delivery and professional services working together. All seven renewed, every one became a reference, and those references were what the big deals were waiting on.

The cost of picking the wrong early wins doesn't show up in your first update. It shows up later.

Michael Watkins, author of *The First 90 Days*, has an image I've never forgotten. Picture a rocket with nothing but a very large first stage. It launches beautifully. Enormous thrust. Everyone is impressed. Then the momentum fades and it falls back to earth, because there was never a second stage.

That's the flashy early win. It goes up, people applaud, and six months later it connects to nothing. By then your reputation has formed around it, and the organization has quietly decided what kind of leader you are.

Your early actions become stories, and those stories get retold long before your results land. They decide whether people see you as the leader who builds things or the one who decorates them.

So how do you tell the wins worth doing from the ones that are merely seductive? Write every candidate on one page: every project, every fix, everything you're weighing for your first 90 days. Then score each one against four questions, zero to four points each, sixteen points in all.

1. Does it move a number the business already cares about? Revenue, cost, cycle time, uptime, retention. Not "will people notice," but "will the number move." Score a zero here and it's out, whatever it scores on the other three. That rule alone clears half most lists.

2. Can you finish it with what you already have? If it needs headcount you don't have, it isn't a 90-day win. It's a 90-day negotiation, which may be worth having, but it belongs on a different list.

3. Does it build toward the goals you've already agreed with your boss? Does finishing it leave you closer to where you need to be at day 90, or is it simply a good thing that happens to be nearby?

4. Will the way you win it change how people behave? This is the one most people skip, and the one I'd fight for. How you win teaches people how you operate.

Once everything is scored, you'll want to do all of it. Don't. Pick three or four. Four is the ceiling, for two practical reasons.

First, a portfolio protects you. Four wins running at once means one disappointment gets covered by a success somewhere else. A single win running alone means one bad outcome becomes your whole first quarter.

Second, and more important: change ten things at once and nobody can tell what's working, including you. Your people can't either. They just feel the churn. You inherited a team that's already nervous about you, and ten changes at once confirms every fear they had. Change comes in waves. You learn, then deliver a first wave of wins, then steady the course, and only then go after the deeper changes.

Then add one question on top of the four, the one that guards against the rocket: what does this win leave me standing on? Two candidates can both be fast and both look good. One builds toward where you're going, and the other doesn't. Take the one that does, even when it's smaller.

Say you're weighing two quick wins. One is a new reporting dashboard the CEO mentioned in your first week. The other is fixing the handoff between your team and support that generates most of your escalations. Both can finish inside 60 days. The dashboard scores well on visibility and poorly on almost everything else. The handoff fix moves a number the business already tracks, and it changes how two teams work together. Only one of them leaves you standing on something.

That's the renewals story in a sentence. Seven renewals were never the impressive choice. They earned the credibility, the credibility bought room to run the bigger programs, and those programs had been moving quietly the whole time.

Smart, capable leaders still pick the wrong wins, and the reasons are predictable.

The first is the first update. There's real pressure to show something fast, and the flashy win is built for exactly that moment. It reads well on a slide. The foundational win often doesn't have a slide yet.

The second is that the easy win feels like control. You can finish it yourself, on your own timeline, with your own team. The right win usually needs other people, and in a new role, depending on people you barely know feels like risk.

The third is the habit that got you promoted. Most technology leaders built their careers on solving problems quickly and personally. In a new leadership role, that instinct pulls you toward wins you can deliver alone, which are rarely the wins that change how the organization works.

The fourth is skipping the conversation with your boss. Question three only works if you've already agreed what success looks like at day 90. That conversation has to come first, and plenty of new leaders never quite have it. They end up scoring their wins against goals they're guessing at, and wondering at day 90 why their boss seems underwhelmed by a quarter that felt productive.

One more category sits outside the scoring entirely: the small irritants people notice immediately. Cut a meeting that shouldn't exist. Shorten one that always runs long. Repair one strained relationship outside your team, the one everybody knows is broken. These score almost nothing on performance, and that's fine. They build credibility in a separate account, they're cheap, and people notice them the same week.

They work because everyone in your new organization is trying to answer one question about you: does this person actually see what's going on here? Cutting a meeting everybody resents answers that faster than any strategy document.

The irritants also tell you whether people think you listen. Ask a few people in your first two weeks which meeting they'd cancel if they could. Most of them will name the same one.

If you're in a new role right now, or about to start one, I recorded a video that walks through this step by step: the four questions, how to score your list, why four is the ceiling, and the renewals story in full. Watch it before you finalize your plan, and if you know someone starting a new role this quarter, send it to them.

https://www.youtube.com/watch?v=3l73iwtKsEo

Your early wins matter far less than what they buy you. So spend your first 90 days building the credibility budget you'll need when the hard change finally arrives.