How Startups Turn a Three-Year Goal Into a 90-Day Plan

Let me ask you a strategic question: Where do you want your company to be three years from now?

• What will your product or service look like? Which new features will you roll out, and how will your business evolve?
• How will your market share expand? Which new markets will you have entered?
• How many customers will you have? How much revenue will they generate? How many employees will you need to support them?

Got all that? Great. You’ve got 90 days.

The future is NOT now

One of the hardest things I have to do, either as a leader or an adviser, is to get my best people to stop thinking three years out and start thinking about today. Don’t get me wrong — these are my best people because they have vision, because they can see the future and are constantly working toward it.

But sometimes these same folks will take a good thing too far. They Luke Skywalker that shit — they can’t stop looking to the future or the horizon, their minds never on where they are and what they’re doing.

I know this type. I am this type. I’ve been in the startup world for over 20 years, and if I look at my failures and my low points, in startup or any other pursuit, the reason I failed wasn’t that I was doing too little; it was that I was doing too much.

The dark side of vision is future-creep

Entrepreneurial vision is a necessary and often overlooked skill. It isn’t about riding trends or wielding psychic magic, it’s about being able to look at patterns today and visualizing tomorrow’s results. In more concrete terms, it’s the opposite of that one dude who just comes in and does his job every day.

But too much vision always leads to future-creep.

With early founders, future-creep usually manifests itself in the overbuilding of infrastructure. I have artifacts to remind me that I’m prone to this behavior, like boxes of old business cards from my previous startups (both successful and unsuccessful). I also have old code, old domains, old social media and SaaS accounts, even (ugh) old relationships, all of them little or no use to me today. But even when I think about those things now, I can’t stop believing they’ll be useful someday.

I can recognize future-creep when I’m talking to someone about short-term progress and I have to interrupt them after they hit their third or fourth tangent. They’re not focused on any one thing; they’re focused on everything, and they can’t stop connecting all the imaginary dots in their head.

Turns out, rhythm is almost as important as talent and vision and execution.

And another trap that catches all entrepreneurs, new and old alike, is not being able to compartmentalize the difference between fundraising activities and revenue activities. I might get yelled at for this belief, but you have to separate the milestones and goals for raising money from the milestones and goals for growing your business. Raising money should always be a future-focused endeavor.

Signs that the future is unraveling

Future-creep manifests itself in constant low-progress activities. For some people, they do nothing but take meeting after meeting, whether or not the meeting has any impact on current milestones, as long as they can pin some future hope to it.

For others, it’s putting too much thought and time into a complex feature that customers aren’t really clamoring for.

For still others, it’s an obsessive focus on revenue and financial projections, running scenario after scenario in dozens of spreadsheets.

The results of future-creep are a lot of promise and a lot to talk about, which feels good and looks like progress. But those results don’t lend themselves to growth. At some point on your road trip, you need to put the map down and drive.

The first step to fighting future-creep is to focus on the future

Let’s fight fire with fire. Yeah, it’s okay. Let’s get all that future focus out of everyone’s system. Let’s get our best talent and our key people in a room and speak directly to our future plans.

Once a quarter.

Schedule a full-day meeting every 90 days with your vision team. These are your key future-state people — it could be executives, or it could be everyone, and it doesn’t have to be the same group every time. It’s all up to you. Plot out the next three years with no limits on what the goals or the metrics are as long as you can draw lines back to today. Have fun with this.

Come out of that meeting with a 90-day plan, and I do recommend that you use “90-day” instead of “first quarter” because it implies that today is day 1, tomorrow is day 2, and the clock is ticking.

Then, over the next 90 days, when projects or requirements or features or goals come up that are out of the 90-day scope, immediately table that thing for the next 90-day session. Now you have a release valve.

Structuring a cohesive 90-day plan

The 90-day plan needs to revolve around three things: Product, market, and customers. Go back to the three questions I asked at the beginning of the post and shorten the time cycle from three years to 90 days. And commit to it.

Those milestones and goals are going to be different for every company, so let me simplify and generalize the rhythm of those 90 days using the example of this very post you’re reading now.

I’ve been writing these two-a-week posts over the last year, and I look at this blog like I would a startup. That’s good for me as a writer (the entrepreneur) and good for you as a reader (the customer).

For the first couple of months, I just plugged away, and it was easy because I was doing it for me, by my plan. At some point — and I totally expected this — writing a new post every couple days got more difficult. Specifically, that point was when I realized I had an audience and that audience was valuable to me. Suddenly I had new expectations, new responsibilities, a reputation to live up to.

Except I didn’t.

Exactly nothing had changed about why or how I was writing these posts except that I could now point to the reason I started writing them in the first place and confirm I was on the right track. This is exactly what happens when a startup finds traction.

So how did I handle the new responsibilities of a growing customer base? I decided to try to get ahead and write a couple posts in advance, so I’d have a comfort level, as well as more time to put more thought into each post. My goal was to sit down each time and consider not only how my post would be received by my audience, but how it would help me grow that audience and tie together with the last post and the next post to make sure I maintained what was now expected of me.

That was a mistake.

Those posts didn’t exactly suck, but that string of work-ahead posts, as well as the extra-care posts that followed — the ones where I had extra time to focus on their purpose — made no difference at all and actually sucked a bit of the life out of my rhythm.

Rhythm is critical, don’t kill it

Turns out, rhythm is almost as important as talent and vision and execution. Good content (product) means content that comes from now, from what I’m doing and thinking while it’s fresh, then listening to feedback from readers (customers), and building that feedback into the next post (release). It’s not static; it’s almost a living, breathing thing.

It’s the same rhythm with your business, release by release, service by service, or customer by customer.

Now, a startup works a little differently than blog posts, but only in terms of time. It’s just a shorter cycle.

I don’t have a 90-day writing plan — I have a 30-day writing plan. Every month, I review the previous month and do my content planning for the next month, making sure it aligns with my long-term goals. Every time I publish a new post, I’ve got three to four days to write another post. From blank white screen to 1,500 coherent, preferably cohesive words. My best content comes out this way because it’s in the moment.

Those three-to-four days are like your two-week sprint or whatever customer delivery cycle you choose.

This is how you structure your 90-day plan. Once you’ve decided on the future, all you need to do is review your previous quarter and do your planning for the next quarter, making sure it aligns with your long-term goals. Then, every time you release a new version or close a new sale or sign a new contract, you’ve got two to three weeks to do the next one. From blank white screen to next version, next service, next project.

Break your releases into sprints, your roadmap into versions, and tackle each sale customer by customer. Always look to the future, but keep your mind on where you are and what you’re doing.

Hey! If you found this post actionable or insightful, please consider signing up for my newsletter at joeprocopio.com so you don’t miss any new posts. It’s short and to the point.

This post originally appeared in Marker -- the business magazine from Medium: https://marker.medium.com/how-startups-turn-a-three-year-goal-into-a-90-day-plan-979c155b2b20