7 Practices to Elevate Your Strategy Execution

Empower your team to succeed by turning strategy into action

Many leaders assume that success hinges on their organization’s strategy. But the reality is, what matters most is how well that strategy is executed. Research backs this up: executing strategy is often more important than the strategy itself (Balarezo & Nielsen, 2017)¹. Even a brilliant plan will stumble without strong execution, while a modest strategy can drive great results if executed with precision and consistency.

In my recent conversations with clients, this theme keeps coming up. As leaders assess their progress and look ahead to the next cycle, they realize the gap between intention and execution. Here are the practices I’ve been recommending to help teams close that gap and make strategy execution a core strength.

While I’m primarily writing this post for leaders kicking off a new strategy execution method, I’m going to try something different and translate the tips for solos and people who aren’t managers but want to be good teammates. By the way, if you find this post useful, be a good teammate and share it with your teammates.

1. Set the Expectation That It’s Going to Be a Long Game

Kicking off a new strategy execution method is a change management initiative. But it’s typically the case that the kickoff of a new strategy execution method is conjoined with another large-scale initiative that’s tantamount to a change management initiative. The exception to this pattern is when a leader realizes that their team or organization doesn’t have the workways and team habits to execute the strategy they previously developed and articulated.

As I said in Team Habits, the concepts of strategy execution and collective behavior change aren't rocket science. The difficulty isn’t what people know they need to do, but getting them to do what they know they need to do. It’s rocket practice.

Execution tends to be more complex and time-consuming than formulation (El-Masri et al., 2015)², which is why so many organizations fail at this stage. Despite its importance, managers often invest less time, energy, and resources in the execution process compared to the initial planning (Bolboli & Reiche, 2013)³. This underinvestment in execution is what frequently causes initiatives to falter before real change can happen.

That said, acknowledge that people are going to be learning new skills, which means they need time to learn and practice those new skills. Take the relatively small recommendation to read 2–3 books. Reading a book as a team, converting the insights into actionable steps for your team, and then putting them into practice will require at least 10 hours per teammate, but likely more. With the reasonable assumption that most teammates are at or over capacity, how and when will those 10 hours fit into their priority stack?

Even this small example demonstrates why so many efforts like this don’t get off the ground. Reading a book is a relatively simple task to complete; a team making the time to read and operationalize the book is a surprisingly difficult task to complete. Shifting team and organizational status quo is an even taller ask. If you’re serious about making the change happen, get real about the long haul and embrace it.

Before we move on, I want to call out that, yes, I know that the new skills and team habits will actually eliminate the Crisco watermelons and fire drills that are both wasteful and demoralizing. It takes time to do said elimination and substitution and this is why I recommend making subtraction a team habit. I often find the capacity for teams to make strategic change happen by subtracting waste and backfilling it with strategic work.

For Solos:

Per the guidance in Start Finishing, if it feels like a truly transformative project or ambitious goal, embrace that it's probably going to take you longer than you think. Plan for 3x the amount of time you think it’s going to take to correct for the reality that this will be one of many things you’re working on. Disregard the 3x rule if you’re willing to truly make this your one thing, but don’t delude yourself.

For Good Teammates:

Rally your team during the slogs of the project, reminding yourself and them that it’s about progress and sticking to it until you’re through it. If you have the trust of your boss, have frank can-do conversations about how long the project may take.

2. Get Everyone a Copy of Team Habits

One of the many reasons I wrote Team Habits was due to years of fielding questions on how to get teammates to participate in and own strategic change. The difference between Team Habits and other books on change management is that Team Habits democratizes change management and enrolls your team into the process rather than forcing your teammates to change. I wrote it as an antidote to the patterns that lead so many change management efforts to fail.

In Chapter 12, I provided the following template for how to report back to your team about how things are going. The four prompts were:

• Here's what we've tried.

• Here's what we've seen happen as it relates to our pain and gain states.

• Here are some of the unintended consequences of what we are addressing.

• Here's what we're working on next.

Because I was writing Team Habits so anyone who wanted to be a good teammate or leader could read and apply the insights, I deliberately chose not to use conventional strategic language because that language can unfortunately signal who “owns” that kind of work.

But I’m sure you see that those are actually questions that prime people to think, communicate, and coordinate about strategic change. It gets teammates to switch their thinking horizon from tasks and projects to the operational and strategic perspective.

Imagine if every member of your organization — whether they’re executives, middle managers, or frontline workers — used that one convention to report progress to each other. That it's not rocket science is a virtue.

That’s just one of many plug-and-play frameworks that your team can play with, break, and make better together, right now. If you sense my intensity here, it’s my “make this a team habit and see what happens” enthusiasm. I love seeing teams and organizations surprise themselves by what they can do.

If you’re interested in buying bulk copies, getting them from Porchlight is the way to go. I recommend at least 20; one set for your team and enough to share with collegial, can-do collaborators from other teams.

For Solos:

Team Habits is actually still for you because you likely have teammates you're not counting. Remember “Poor Team Alignment” from the Air Sandwich in Start Finishing? Team Habits helps with that. :)

For Good Teammates:

Buy two copies of Team Habits — one for yourself and one for your boss. Put notecards or sticky notes from 3–5 relevant rocket practice sections of Team Habits into your boss’s copy, then ask her if she's open to your leading the team through those rocket practices. If she's into it, figure out how to make a bulk buy of Team Habits for your team so everyone has the manual. You can help your team work better together just as well, if not better, than your boss.

3. Use OKPs to Keep the Conversation Focused on Objectives and Key Results

Teams have a habit of getting project locked and/or pulling the conversation into projects, especially when progress on goals isn’t happening. Everyone has experienced the dread of higher-level conversations getting in the weeds of projects, tasks, bean-counting, and word-smithing, and I’m also pretty sure that everyone has realized when they've been the one who’s led the team down 18 rabbit holes.

OKPs are my modification of the well-known OKR methodology. I’ve modified it to Objectives, Key Results, and Projects because of the tendency for people to make projects into key results, which all too often makes what would be strategic conversations turn into project update and problem-solving conversations. Teams will chew up hours talking about how to do projects without reflecting on whether those projects are driving objectives and key results forward.

Adopting OKPs gives teams a framework and language to call out when they’re in the project horizon rather than the operational and strategic horizon. It gives leaders a way to easily pull the conversation back to the strategic and executive horizon rather than falling prey to the accidental micromanagement of projects. It also gives everyone a way to identify if they’re needing project support and collaboration or more context, perspective, and articulation of strategic issues.

I have a whole post on how to use OKPs, but even just introducing the framework can do a lot of work to help with the goal-setting and coordination parts of strategy execution.

For the rest of the post, I’ll use objectives and key results. Translate those into MITs, WIGs, BHAGs, GTS, KPIs, or whatever acronyms work with the strategy execution framework your team and organization uses. I’m biased to OKPs, but I’m not a zealot about it.

For Solos:

Use key results as the filter for what projects are worth starting and continuing. If you can’t tie them to a key result, you might have a Bright Shiny Object in your hands. And if it’s not getting you a key result, you’ll need to figure out if you’re doing the right activities poorly or just doing the wrong activities.

For Good Teammates:

Help keep your teammates focused on the key results rather than getting target-locked on projects. Remember that doing more projects is rarely the best way to make the most progress on key results; doing fewer of the right projects usually is.

4. Make Your Cadence of Communication About Goals Your Non-Negotiable Team Habit

With strategy execution, continual communication about progress toward strategic goals is the key unlock.

Win, lose, draw, or recalibrate, you have to talk about the scoreboard frequently enough that you can determine whether you're running the right plays or playing the right game.

Quarterly is not frequent enough. Monthly probably isn’t, either.

The frequency of communication determines how long a team or organization can drift. Given most organizational realities, a quarterly communication cadence means that an organization can easily drift for 4–6 weeks of a quarter. There's some “oh yeah, we were supposed to be working on that” time before the quarterly review and some “oh damn, we need to reprioritize projects” time after the quarterly review. This means that, in a given year, your team or org may spend at least a quarter drifting, before you take into account seasonal trends like summer PTO and the holidays.

This is especially important given that research shows that 95% of employees often don’t understand or are unaware of their company’s strategy, contributing to poor execution results.⁴ Without regular, clear communication, strategy execution efforts will falter because people won’t be aligned on the objectives, the "why," and the progress being made.

The more cross-functional and transformative a strategic initiative is, the longer the drift cycles are as conversations work up, down, and across all the echelons. Tighter communication cycles are a forcing function to weed out unnecessary conversations while still ensuring the strategic priority remains the priority.

Of course, there is such a thing as too-frequent conversations about strategic progress. Daily and weekly is likely too frequent for mature organizations, but might be perfect for startups. As I said in Team Habits, team communication habits are often about tuning the different knobs to the right frequency, depth, and tone that works for your team and organization.

You're likely going to choose the wrong goals, whether it's the scale of those goals or the direction of those goals. That's okay, as long as you're talking about the whys underneath it.

For instance, you may set a sales target (key result) like “increase sales by 40%” because growth is a momentous strategic imperative that your organization needs to build toward. Down the road, you may figure out that that goal actually needed to be 55% or that it actually should've been “Increase net new business by 20%.” Your organization may also figure out the real problem wasn't revenue, but profitability.

Continually talking about strategic goals and how they relate to what's important to your organization will help you figure out what you should really be focusing on faster. In the example above, it's much better for folks to figure out that net new business or profitability was what needed to be prioritized a half-year or year(s) earlier rather than resourcing and building toward other efforts.

Talking about strategic goals doesn’t have to take long, though. It could be as simple as keeping them on the top of meeting agendas and asking if anyone has any significant progress updates. Senior leaders can ask their managers how they’ve translated the goals to their teams. Teammates could ask if any OKPs are especially interesting to their teammates.

Continual conversations don’t need to be hard, thorough, or a Thing to do. The more they’re simple and baked into routine conversations, the better.

For Solos:

Keep your OKPs front and center and return to them when you're doing your weekly and monthly planning. Be careful about having them nested in umpteen levels of Notion/Google docs and know that static information presented on screens starts to become noise that your brain filters out rather than pays attention to.

For Good Teammates:

Be the champion that surfaces and points to OKPs during meetings, project planning, and prioritization conversations. Volunteer to be the goal coordinator rather than making it your boss's job. If you care about it, own it.

5. Tie Operational and Project-Level Wins to Objectives and Key Results

All too often, teams and organizations are completing projects and creating momentum that align with objectives and key results. But because they're so project-locked and strategic thinking can be hard to do and make time for, those small- and medium-sized wins aren't being bubbled up and counted as progress towards objectives.

And since those wins are being bubbled up, people tending and watching the strategic scoreboard often think nothing's happening, people aren't moving fast, or people aren't prioritizing strategy execution. In the absence of information, people make up stories and they're typically not good. This is as true for leaders who should know better as it is for everyone else.

Per the usual, so much team and organizational tension is a symptom of poor team communication habits and org communication workways. Also per the usual, it's hard to over-index on communication, especially about how the week-to-week work is driving strategic progress.

There are two simple but powerful ways leaders can tie tactical progress into their OKPs:

1. “Catch teammates in the act” and celebrate that the work they just completed or reported on ties to OKPs. This one goes so much further than leaders think it does because a sincere and specific good job is often hard to come by.

2. Ask teammates to think about how the work they just completed or reported on ties to OKPs. Make sure to intone the question so that it’s curious and leading rather than critical. If you’re asking via text, use emoji to give mood context, as in 🎉 🙌 “In what ways does this tie to OKPs?” 🚀 (My team would understand that I’m excited and curious from that string of emoji  and not 😠💩🔍.) 

Yes, this is a bit of an extension of #5 above, with the main difference is that this is looking up from the work rather than down from the strategy. Teams and orgs need both approaches and perspectives in play if they want strategy execution to become a core competence rather than some edge expertise that they sometimes deploy and sometimes don't.

For Solos:

Create a win log (it can be digital or physical) and at the top of the page (or every few pages), rewrite your OKPs so that they're visible as you’re capturing wins and you can tie your wins to those OKPs. How did that big task or project you just finished relate to an OKP? What key result might it have moved forward?

For Good Teammates:

Ask your team for the wins of the week and tie those wins to your OKPs. Compile them into a format that works for your boss to see and mobilize with her peers and boss. Don’t let your and your team’s wins die in the ephemera and chaos of the workweek. 

6. Read Zone to Win if You Have Multiple Business Units with Different Degrees of Maturity

It’s well known that mature organizations strangle the startups and scaleups they spawn.

It’s incredibly hard for managers of a mature organization — typically with much larger numbers, stake, and scale — to switch modes and operate as part of scrappier, messier entrepreneurial ventures. Managers of mature organizations are largely seeking efficiency and continuation of an existing model of delivering value; managers and operators in startups and scaleups are trying to figure out what the actual model is and how to build around it.

If you’re the leader of the startup or scaleup, you'll need to continually remind your boss and peers that your business unit is a startup or scaleup with different rules in play when your boss and peers expect your very ugly duckling to swim like the rest of the ducks. They’ll forget you’re a swan.

If you’re a leader who has a startup or scaleup mixed in with other more mature business units, you’ll need to remember that you may have a little swan on your hands rather than another duck. Your startup’s long-range planning window may only be two quarters, whereas your mature businesses may be two or three years. Your startup may not have been profitable for the last two years and that won’t matter, just as your scaleup’s sudden need for cash for talent may not have fit into their annual budget.

Zone to Win is a short-ish read that will help you and your teams think through the different needs of your startups and scaleups, as well as how to resource them. By giving some common frameworks, it’ll facilitate fruitful conversations without a single leader trying to codify those frameworks.

For Solos:

You can probably skip reading the book, but the key takeaway for you is that you’re starting new and it’s going to be messy. If you’re used to excelling in a mature organization with a lot of organization, resources, and support, be prepared to struggle as you have to fix the plane while flying it. If you’re starting a business, The Small Business Life Cycle is a more relevant read — embrace Stage 1 and 2. :)

For Good Teammates:

If you’re in a startup or scaleup in a mature organization, remind yourself, your teammates, and your boss that the team habits you need to cultivate for your business unit may look a lot different than the team habits and org workways of the mature organization. And if you’re part of the mature organization and interact with folks in the startup or scaleups, have patience and compassion for the folks who are making it up as they go along and be curious about what they’re doing that might work well for you and your team.

7. Present from Your Work Management Tool

Part of what often makes talking about strategy execution is that doing so requires additional meta work like compiling completed projects into a deck, spreadsheet, or writeup. A piece of that meta work is inevitably chasing teammates down for updates or teaching teammates how to understand how this completely different tool or perspective ties to what they’re doing.

The larger the organization, the more likely that that kind of meta-work is inevitable. But teams and more streamlined organizations can eliminate a lot of it by presenting from the tools they work in.

For instance, Asana has done OKPs right. If your team is already using Asana, their goals and portfolios feature allow you to track, communicate, and present right from Asana — no extra spreadsheets, emails, and decks required. One of the reasons I recommend Asana to teams who don’t have a work management tool is because it can grow with you as you and your team grow in your strategy execution capabilities. In the beginning, it can be a shared to-do list; in the end, it can be your whole-org strategy execution engine.

Other work management tools allow you to do this, too, with different degrees of up-front building and/or external consultants to get there.

As I was discussing getting her OKPs into Asana with a client, I commented that I knew it was going to take some work to get the structure of her work into Asana. She quickly responded, “I’m going to be building something one way or the other — I’d much rather it be in the tool we’ve worked to get our team to adopt and that they’re already using.”

Her response conveys it all. I captured it a few weeks ago, not knowing that I’d be writing a 4,000-word post with tidbits of other conversations, too.

For Solos:

If you’re already using a tool like Momentum, Asana, or our Momentum Planners, this tip is covered by (4) and (5) above. If you’re not and have a collection of stickies, notebooks, or random docs, it’s about taking some time to cross-relate and organize them so you can actually see what you’ve done.

For Good Teammates:

First, be the teammate who actually tries to use the work management tool or create something else that works for your team. Second, if your team does status updates, ask your boss if you can just share your screen from your work management tool that shows how your tasks and projects tie to OKPs. Once your teammates see you do it — and it becomes less work to do than to pull those tasks out — you may start a team habit around it.

Recap

The bottom line is that strategy execution is what separates winning teams from those that struggle. It’s not enough to just have a great strategy on paper — you’ve got to take the long view, commit to the work, and empower your team to actually get it done.

In other words, it’s about making strategy execution a habit, not a one-off event.

The good news is that your team is already executing a strategy, even if that strategy is “balance all the incomings and try to keep our jobs.” Your job is to guide them in getting on the strategy.

Get to it. :)

p.s. If you’d like some expert guidance on how to get to it, let’s see how working with me can be a part of your strategy execution strategy.

1. Balarezo, J., & Nielsen, B. (2017). “Scenario planning as organizational intervention: an integrative framework and future research directions.” Review of International Business and Strategy, 27(1), 2–52.

2. El-Masri, M., Tarhini, A., & Harfouche, A. (2015). “Factors affecting the strategic business-IT alignment: a case study of the banking sector in Lebanon.” International Journal of Electronic Customer Relationship Management, 9(3), 224–252.

3. Bell, B. S., & Kozlowski, S. W. J. (2010). “Active learning: effects of core training design elements on self-regulatory processes, learning, and adaptability.” Journal of Applied Psychology, 95(5), 848–859.

4. SpringerLink (2021). “Awareness of strategy execution barriers in decision-making process: Moderated mediation analysis.”