Welcome back, aspiring and current Chiefs of Staff!
In this week’s issue, we’re featuring guest author Dreams with Deadlines (DwD), the strategy meets execution community (more on them at the end of the issue). DwD is a global network of strategy and operations leaders who are passionate about using OKRs and agile practices to achieve audacious goals and build a better future.
With OKR programs typically falling into the Chief of Staff remit, a community like Dreams with Deadlines can be super valuable to help navigate the nuances of OKRs, and optimize your program with help from experienced peers.
So, if you could use a little extra inspiration and support in your strategy development & OKR adventures - Dreams with Deadlines is worth checking out (plus it’s free to join!)
*Interested in sponsoring a future issue of Ask a Chief of Staff, hit reply!
How can a Chief of Staff avoid the most common OKR Pitfalls?
OKRs are deceptively simple in concept, but not easy to execute. Once you begin the implementation process within your organization, you realize they take committed effort, clear guidelines, and ongoing adjustment.
In this week’s issue, we explore three common pitfalls that organizations run into and how you can effectively avoid them. This issue is an excerpt from DwD’s OKR Program Failure-Prevention Guide - make sure you read the full guide for even more pitfalls and expert tips!
🕳️ Pitfall #1: Jumping immediately into “We’re doing OKRs”
Sometimes organizations implement OKRs for the wrong reasons. They may not understand the method or the goal of OKRs or they confuse it as a replacement for other methods, like performance management.
“For the wrong reasons” OKR scenario
📸 Picture this: Jessica, a Chief of Staff, devours a copy of Measure What Matters over the weekend. When she returns to work, she gathers a few folks from her team and shares, “I read this great book. We should do this OKR thing.”
Her team scrambles to figure out what this means and how to make OKRs happen, using their own copies of the book as reference. Eventually, executives ask all employees to craft OKRs without proper justification or training. No one knows why they’re supposed to do this, and everyone thinks it’s another way for leadership to ask for more reporting.
💕 A better way
OKRs are about turning good ideas into great execution. They provide a common language to articulate your goals, track and measure progress, and reassess priorities. They encourage autonomy, ambitious outcomes, and cross-functional collaboration. Every organization might have a different reason for why they use OKRs — the key is to have a compelling one. Establishing the “why” for OKRs before jumping into the “how” will set your company up for success better than jumping in headfirst.
If your organization is looking to implement OKRs for the first time, don’t only rely on your internal team. You can look to resources like Quantive or hire external OKR consultants to guide your team through its first iterations. Once you get the hang of it, then you can look to taking the process in house.
Expert tips
Create a strong why statement. Author Simon Sinek suggests this simple framework:
To [insert contribution], so that [insert impact].
Here are some good why statements:
To strengthen communication, so we can break down silos
To increase focus and alignment, so we can maintain market leadership
To improve accountability and evaluation, so we can keep our customer promises
🕳️ Pitfall #2: Not having a strategy
According to Roger L. Martin, strategy is a set of five choices for winning. For OKRs to work best, you need a strategy.
“The empty strategy” OKR scenario
📸 Picture this: Linda, an executive coach and OKR expert, discusses an OKR implementation project with her new client Doug, the COO of a manufacturing company.
In the meeting, Linda says, "If I asked you to share, the most updated company strategy document you have, what would you send me?"
Doug pulls up a spreadsheet containing the budget and something resembling a Gantt chart, then walks Linda through the document. Linda now realizes this client engagement just grew beyond OKR implementation.
💕A better way
Don't confuse strategy with planning. Strategy is a set of integrated choices. OKRs provide a plan of execution toward that strategy. Without a strategy, OKRs risk becoming unfocused statements such as "Increase sales" and "reduce costs." In such cases, they may not be worth the effort.
Expert tips
Have a strategy in place, and make sure your strategy provides clear direction as an OKR foundation. Reflect on the questions from Roger Martin's Strategy Choice Cascade:
What is our winning aspiration?
Where will we play?
How will we win?
What capabilities need to be in place?
What management systems must be instituted?
Refer to his Strategy Choice Structuring process or your own method of strategy development. Keep any strategy documents under five pages, as anything more is morphing into strategic planning territory.
🕳️ Pitfall #3: The Big Bang approach to OKR rollouts
OKRs involve change management — you’re asking everyone to operate in a new way. But while managers may view change as an opportunity to strengthen the business, teams may view it as disruptive and intrusive.
“Everything, everywhere, all at once” OKR scenario
📸 Picture this: Marcus, a department head, learns about OKRs and thinks it’d be great for his teams to adopt them. He meets with the executive team, gets buy- in, and starts a company-wide OKR rollout, but doesn’t consider how this change will affect employees.
During this time, his company is working towards a big seasonal event — everyone is heads down and focused. While Marcus has great rapport with his teams, they think the OKR initiative is a distraction and ignore it. It seems like a fine idea, but it’s not a priority because everyone’s focusing on a demanding project. No one engages or connects with the purpose of OKRs, and Marcus’s implementation fizzles out.
💕A better way
Keep context in mind and approach your OKR initiative incrementally.
You may get excited when you see positive results from a proof of concept. But concepts may fail to show you the planning, consideration, and timing it takes to see OKRs succeed.
Refrain from doing too much, too fast, especially without team buy-in. Forceful adoption will yield lackluster engagement — you need to connect people with the purpose behind OKRs.
Expert tips
Avoiding the Big Bang approach involves doing your due diligence, for the methodology and your teams.
Ask questions
Why OKRs?
Why roll out now?
Why not later?
How will we track our progress?
How do we define success? Be specific.
Secure executive buy-in
Have senior leaders review your plan. Show them what change looks like. Explain the steps you'll take to ensure success. Get an executive sponsor to support the program actively.
Start with a proof of concept
Begin with senior leadership, a pilot department, or pilot team. Educate and train. Have the right advisors and coaches on board. Celebrate wins and develop internal case studies. Recruit knowledge replicas (i.e., OKR Champions and Ambassadors) to help drive change.
Simplify and scale up
Bake OKRs into existing meetings and rituals. Make sure to review, discuss, and track for impact. Expand to more teams and departments gradually. Each group will need about three cycles. Expect to tweak and learn as you go.
Explore them all...
These are just a few of the common pitfalls explores in the DwD’s OKR Program Failure-Prevention Guide. With a bit of experimentation, you’ll eventually develop your own winning solutions. But you don’t need to rely on trial and error alone!
Whether you’re new to OKRs or a seasoned pro, the Dreams with Deadlines community will give you the knowledge, connections, and resources you need to achieve your goals with greater confidence, efficiency and impact.
Hope you’ve enjoyed the latest issue of this newsletter and we’re looking to you for future newsletter topics! If you have any questions around being a Chief of Staff, tactical takeaways that you can apply, or other curiosities about the Chief of Staff role, submit a question below and we’ll answer it in a future newsletter issue:
🎥 Upcoming Workshops:
June 15th: Fireside Chat with Leigh Felton - Author of Unlocking Your Inner Chief of Staff
June 20th: Using Soft Power to Lead - Seisei Tatebe-Goddu
As a reminder, workshops are free for all Ask a Chief of Staff community members and the recordings will only be provided to members and registered guests. There is a suggested ticket price on all workshops on but the first 25 registrants can waive your ticket price with code ASKACOSREADER.
Additional Chief of Staff Related Reads:
Comms Strategy and Tactics for Startups
What does a Chief of Staff do in an early stage tech startup?
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👋🏼 Until the next issue,
Clara
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