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Fewer "to do's," better results

How coaching OKR goal-setting has rewired my brain

Sara Lobkovich
Sara Lobkovich
9 min read
Fewer "to do's," better results

Happy very nearly new year, friends.

If you’ve seen me professionally in the last few months, you’ve already started the mental countdown on how long it will be before I say “OKR.” There you go. It’s out of the way.

If you’re one of my “personal life” readers and/or don’t work in a corporate environment, skip down to Why I’m obsessed with OKRs to see how this framework is helping me think about, set and achieve my own goals differently.

For those of you who work in or with corporate environments, keep reading.

The strategic planning gap

In my consulting and leadership work, I’ve done a LOT of strategic planning work with groups and teams, and there’s usually three orientations represented in most room:

  1. Lots of people who think in terms of activities: “We need to build a marketing plan by Q3.”
  2. A few people who think in terms of directions or goals: “We need to increase our sales.”
  3. A few people who think in terms of measurements: “But how will we measure success?”

They tend, during planning exercises, to talk across each other, with a palpable lack of alignment in the conversation. Before exposure to the OKR framework, facilitating that planning exercise was typically a messy process of trying to work the room toward agreement on a direction or goals, and then to agree on a set of activities or commitments, completion of which means success of the plan. That approach often left gaping holes in decision criteria and did very little to achieve actual alignment among the different orientations in the room. As a systems thinker and alignment-seeker, there was lots of work for me to do, but it was rarely energetically satisfying.

I could write a book about my year of slowly and fully assimilating to Objectives and Key Results-based goal-setting but I don’t have to — it’s right here.

So instead, here’s a quick introduction to:

  1. what OKRs are,
  2. why I can’t stop talking about OKRs, and
  3. a few tips I’ve developed along the way to help clear up some of the initial challenges in crafting OKRs.

What’s an OKR?

The Objectives and Key Results (OKR) goal-setting and management methodology born at Intel and has been adopted by Google and many other tech and non-tech organizations. Here’s one version of the origin story.

The short version: Objectives and Key Results creates a structure for goals and implementation plans that helps align organizations and teams from the top down, bottom up, and across the organization. Here are a few of the standard definitions from the experts:

From Workboard (an enterprise OKR solution):

And from the Measure what Matters website:


“An Objective is simply what is to be achieved, no more and no less. By definition, objectives are significant, concrete, action-oriented, and (ideally) inspirational. When properly designed and deployed, they’re a vaccine against fuzzy thinking—and fuzzy execution.”

Key Results

“Key Results benchmark and monitor how we get to the objective. Effective KRs are specific and time-bound, aggressive yet realistic. Most of all, they are measurable and verifiable. You either meet a key result’s requirements or you don’t; there is no gray area, no room for doubt. At the end of the designated period, typically a quarter, we do a regular check and grade the key results as fulfilled or not.

Everything else

Everything else is a supporting activity. Activities are called different things by different authors (some writers call them “initiatives,” or “projects”) — they don’t get a lot of attention in Measure What Matters. They’re also the place where the majority of people start and finish their thinking: what do I / we have to do?

And even in the early OKR workshops I participated in and facilitated, the room tended to stay in “everything else” land. Elevating into directional, aspirational or inspirational thinking requires trust, and comfort with collaboration that isn’t present in all teams. And Key Results were a real struggle for most workshop participants: setting any kind of measurable goal felt “scary” or impossible because they didn’t control all the variables for success.

But even with the friction, there was still something there. I found myself embracing the path of least resistance — letting groups focus on tasks — and then asking questions:

  • Does that activity ladder up to a bigger goal?
  • Does this group of activities actually align to a larger objective?
  • How could that be measured?

Sometimes I did it in the room, and sometimes I’d sit down afterward with the workshop outputs and try to make sense of it myself. Those early frameworks weren’t awesome, but they were better — more aligned — than the plans I’d built in the past. It was enough to get me building a bigger toolkit of questions, that then I started to see applications for almost everywhere.

I started working with OKRs myself to plan my own work (and ultimately, personal goals) and that’s how I became OKR-obsessed.

Why am I obsessed with OKRs?

I’m obsessed with OKRs, personally, because I’ve been in activity-based environments for the last several years: for the lion’s share of my work, the answer to the question “How will we measure success of this?” has been “client satisfaction” at best and “client happiness” at worst. And there is nothing wrong with that: a huge amount of consulting work is being hands for clients who need them. But when I started interrogating my work with the question:

  • How will success be measured here? and
  • How will I measure success here?

I realized that I was craving work with actual, measurable impacts and outcomes. I was craving work with a bigger “why:” with accountability, and with consequences, and where reasonable people can disagree about the details of the “how” but agree on what success looks like in the end.

As a coping mechanism I started developing my own OKRs for my work. Officially, the measure of success was client happiness (did I do the work the way the client wanted / would have done it?). But in addition, I’d map out my own objectives and key results as measures of success and then set up my client work with them. So even if the OKRs weren’t coming from the client, I’d suggest them myself, and use them to try to ensure alignment with client expectations. In situations where I had trouble reaching “client happiness” I could look at my own OKRs and see that I’d done what we set out to do, and keep that as a touchstone while trying to work the work to client complete, without overworking the work based on my own anxiety / insecurity / imposter syndrome / what’s wrong with me that I can’t read the client’s mind and get this right?!

Focusing on objectives and key results (and what activities support those key results and objectives) in my own work helped me ultimately set new personal objectives during the second half of 2019:

My objectives for my work were

  • to spend more of my working time experiencing “flow,” and
  • to shift my work from mostly measured by activity output to mostly measured by impact.

That sounds so simple, but the impacts have been potentially (actually) career-changing. As we wound toward year end with my most recent consulting agency those objectives made it an (emotionally incredibly hard but also objectively) easy mutual decision to change the nature of my employment from full time W2 to project-based so that instead of me working whatever work was needed to be covered, I and we can pick and choose the work that’s in my actual wheelhouse and highest and best use. That’s freed me up to explore other possibilities that may be a more frictionless fit for me; and it’s also given me a killer set of questions for my interviews and informational meetings. When I speak with potential clients and/or potential hiring managers and ask about how they measure success of the role or work we’re discussing, I’m listening extremely closely for either:

  1. a clear enunciation of how success will be measured, even if it’s imperfect; and / or
  2. a willingness to engage in a meaningful conversation about how success will be measured.

When the answer indicates that the role or engagement will be activity-based, it’s now really easy for me to refer that work elsewhere since I know I’m not the best resource for it.

How to get started

There are a ton of links in this post to the What Matters websitethe book’s obviously a great starting place and they’ve got a lot of great resources on their website.

Workboard, a maker of enterprise software for OKR deployment that I’m now also utterly obsessed with (it solves the problem of tooling for widespread adoption and alignment in large organizations) also makes killer OKR content including:

And even with all of that, the more times I worked through OKR workshops with clients, the more I felt like there was still a tool missing. What I craved was an OKR builder: something to help people who were struggling to understand how to elevate their thinking to the level of Objectives and Key Results, and struggling with what the difference is. So I built something to help fill that gap, and I wanted to share it with you.

Here it is: a worksheet of building blocks for Objectives & Key Results.

So many of us are mulling over New Year’s Resolutions and/or themes for the upcoming new year. I’m not a Resolutions gal myself, but I do check in with myself on occasion to make sure I’ve got direction.

The vision I have in mind for 2020 is still crystallizing, but it revolves around love, wisdom and worth. Spending more of my time being love and working with love, and listening to and honoring my wisdom and seeking out new-to-me wisdom from others. Spending more of my time on things worth caring about; and spending more of my time in places that help me remember my own worth.

And that vision will flow into objectives, key results and activities that shape how I spend my time in 2020 both personally and professionally. And the activities that I just have to do — that are actually my work and not delegatable to someone else, even if I don’t love them — they’re not arbitrary and meaningless “maintenance” must-do’s. I can mentally arrange them into this structure: those activities support my OKRs, and can be done with my vision for the year in mind. I guess this is just another way of being mindful and present: and as the clock ticks toward midnight on this decade, I’m really grateful for the totally unexpected presence and mindfulness that’s come from this one, simple but not easy, goal-setting framework.

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Thank you so much for reading, and for the words of affirmation that have trickled in after every nervous press of the publish button since November. I’m enjoying the rhythm of this: of (Objective) holding myself accountable to creating, with no excuses, every other week (Key Result).

And now: I’m unplugging to ring in the new year and new decade. Have a safe, fun, happy holiday and I’ll see you in 2020!

PS: If what you’ve seen here (or here or here) piques your interest (even if it sparks more questions than answers), I’d love to get on the phone for 30 minutes to hear what you’re working toward for 2020 and see if I may be able to help or point you in a helpful direction. The link below takes you to my robot meeting scheduler: she’ll take care of the calendar wrangling.

Let's chat

Now’s the time: I’ve got more flexibility in January than usual, and am excited to to fill some of it with serendipitous connection. I look forward to speaking with you!


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