Bootstrapped startups and the shit I learn in therapy

Early this year, I felt my motivation slipping. I was feeling overwhelmed, discouraged, and my excitement for the business was gone. I couldn’t get it back.

Something had to change. So one day I blocked off 2 hours with my therapist, and we sat down to talk about goal setting.

You see, I’ve found that my therapist is excellent at solving business problems, better than any of the business coaches I’ve worked with. Turns out that most business problems are really just people problems. Which is exactly what therapy is all about.

But let me rewind.

When we first discovered OKRs years ago, it felt like we had unlocked a new superpower as a team.

OKRs (Objectives and Key Results) are a goal-setting framework that boils down to a few guiding principles:

  • Objectives are the qualitative goals that make your team feel excited to get up and go tackle their work.
  • Key results are the quantitative goals you use to measure whether you are reaching your objectives.
  • From our reading Key results should be hard enough to reach that you fail about 50% of the time. Some people recommend a target success rate of 70% instead, meaning you make it to 70% of the original plan.

The year we implemented OKRs was our first profitable year. It felt like we had a new focus and energy; we were making steady progress and the business was improving.

One set of OKRs from when our goal setting was really humming and we were making regular progress.

That’s what goals should do: they should help you see a path to progress and align the key members of your team towards the same purpose.

And that’s what OKRs did for us… for a while.

Then as we grew, things started to change. We always set OKRs for the quarter, but we regularly found ourselves getting a couple of weeks into the quarter and learning some new information that had us wanting to throw out one or more goals. It became hard to figure out who to include in goal setting and how to include them; our goal-setting felt rushed. And inevitably, we often ended up with a bunch of sales or marketing goals (our marketing team was me and a couple of freelancers) and maybe one for our production team (everyone else in the company).

We started to feel like we were stumbling around talking about goals, but not doing much with them.

That went on for most of 2020. Then, at the beginning of 2021, we dropped OKRs completely. We set a few year-long goals but stopped worrying about quarterly OKRs... but that didn’t feel like it was working either. We weren’t making much progress towards those yearly goals.

Which brings us back to that 2-hour conversation with my therapist about goal setting.

Here’s what I learned, and what we’re putting into place at Krit. Many of these points may seem obvious, but they have been extremely helpful for us—so maybe they will be for you as well.

What makes a good goal?

There are at least four elements to a great goal. Three we knew already, but there’s a fourth we were missing and I don’t see talked about often enough.

1. Challenging, but achievable

While I’m not sure I agree with our original measurement that you should miss your goals 50% of the time, a good goal does need to be challenging enough to push you. Otherwise, it starts to feel too much like a task.

Plus, if your goals aren’t challenging, you don’t feel nearly as much satisfaction when you hit them. Which leads to our next element.

2. Motivating

Humans have a lot less self-discipline than we think we do. If a goal isn’t interesting or exciting, we’re much less likely to make progress.

This is where team feedback (or at the least a strong dose of empathy and a sense of what your team cares about) is super important. Because your team is not different from you: they need to be motivated to make progress too.

3. Measurable

This one shouldn’t be a surprise: if you can’t measure it, how will you know when you get there? But measurable doesn’t have to mean cold, hard data. Sometimes a valid measurement is something like:

  • Do the results of the interviews match up with our survey?
  • Do the founders agree we achieved this?

4. Tied to one or more projects

As my therapist and I dug into why our past goals weren’t working, I remembered Tiago Forte’s PARA method. PARA is a system for organizing digital information that breaks all of your info into 4 categories:

  • Projects
  • Areas of Responsibility
  • Resources
  • Archive

Tiago has a rule. Goals have to be tied to projects, because “a goal without a corresponding project, that’s called a ‘dream.’”

In our previous goal-setting process,, we were giving very little thought to how goals would get accomplished. We weren’t outlining the necessary projects, so our goals were really just dreams.

Take the goals we set at the beginning of this year:

Our original 2021 goals

Clearly, to improve client satisfaction we needed a way to measure where client satisfaction is now.which will first require us to research how other teams measure it. But we weren’t putting in the work to define the requirements for this project: we weren’t staffing it or creating a project plan, or even discussing how much time we could allocate to it.

We do a great job of all those things when we start a new client project, but completely failed to do them when setting goals for ourselves.

9 questions for evaluating goals

We’ve developed a set of questions to help us identify whether a potential goal has the qualities of a good goal. The astute reader may note that a lot of these really come back to, “is this ACTUALLY achievable?”

  • Have we done this before?
  • Who is going to own this goal?
  • Who else will be involved?
  • What is involved in accomplishing this goal?
  • How much time do we estimate that will take?
  • How much time do we have?
  • What barriers do we see?
  • Is this realistic?
  • Does this goal cover the whole team?

That very first question has turned out to be super important. Have we done this before? We’re often setting goals that take us into uncharted territory, but we treat them like all the others, which doesn’t make any sense. Doing things you’ve never done before is inherently harder.

So if the answer to this question is NO, then we need to assume we’re going to get it wrong. And if we’re going to get it wrong at least once, then what we’re really doing is running an experiment. If you remember your 6th-grade science class, when conducting an experiment you:

  • Develop a hypothesis
  • Design a test
  • Take time to measure and analyze your results
  • Rinse and repeat

Here’s the lesson we learned: without building in time for experimentation, any time you set a goal for something you’ve never done before you’re going to drastically underestimate the time required to be successful.

Who should set our goals?

Once we started to define parameters for a good goal, the next question I had was, “who should set these?”

Historically we had tried to set goals as a team: everyone came up with ideas and we voted on those together. I wanted to make sure people felt bought in, felt like a part of the process.

But at the same time, my job as the CEO is supposed to be to set the direction of the company. Am I doing my job if we’re voting on it? Does making decisions as a committee run the risk of diluting the end results?

So who should set goals? The answer we landed on is, it depends.

There are, of course, different levels of goals. Company goals determine the direction of the entire company. For us, these should be set by the partners (at Krit, it’s Austin and myself) with feedback from the team. We have the most context, the most at stake, the longest view, and perhaps most importantly the most time to think about goals.

Team goals determine the direction of a team. These should be set more collaboratively with direct input from the team, and then finalized by the team’s manager. We are still at the size where we largely operate as one team, so for now we won’t be setting team-specific goals.

Individual goals help guide each of our individual efforts. These should be set by each person on the team, with feedback from their manager if they want it.

How often should we set goals?

My final question was, “how often should we set goals?” And again, the answer we landed on was: it depends. Just as we have different levels of goals, using different time frames helps to give us a mix of high-level views and practical targets to get there.

1. Long-term

Long-term goals give you and your team an idea of where you’re going. What does success look like? What are we trying to achieve? For us, 3 years felt long enough to give us that high-level view but short enough it wasn’t too foggy.

2. Mid-term

Mid-term goals help paint a picture of what you need to do between now and then to start making progress towards your long-term goals. They start to break down the process of what you’re going to do to get there. For us, this is 1 year.

3. Short-term

Short-term goals give you an idea of what you need to focus on now. They need to be long enough you have time to make progress, but short enough they aren’t constantly changing. We’re sticking with 1 quarter (3 months) for short-term goals.

Our work-in-progress goals

If you’re like me, all the blog posts in the world aren’t helpful without real examples. Here are our work-in-progress long-term goals.

Long-term (3 years)

  • Accounts can be closed, managed, and grown without a partner - Client Success / Operations
  • 30% profit margin - Finance / Operations
  • 5 highly qualified candidates in 4 weeks per job posting - Recruiting
  • Average 6 months of filled capacity, with 75%+ cybersecurity - Sales
  • Measurably high team satisfaction - Ops
  • Everyone in the company can explain *the Krit way* for their role - Everyone

Notably missing are goals directly tied to design and engineering (we’re trying to figure out how to incorporate those). Also, some of these are better defined than others: 30% profit margin is pretty clear, but ‘measurably high team satisfaction’ needs work.

Again, these are work-in-progress. Austin and I are meeting for an entire day once a month to work through these goals and improve them. We’re then sharing them with the team at our monthly All-hands meetings to collect feedback.

And yes, I’m running them by my therapist.

What are your goals? How does your process differ from ours?

This post originally appeared on the Krit blog. Header photo by Terrance Raper on Unsplash.

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