Strategic Planning That Actually Works

Farrar Frazee
Mar 11
6 min read

Annual retreat, strategic planning meeting, year-end meeting, leadership regroup. So many names for the same, tired gathering of beleaguered but hopeful leaders, setting the path for the year ahead. We bring our ideas, our aspirations, our goals, maybe cascaded from our CEO or board leadership or maybe not, and we make some pretty plans and feel great about all we’ve accomplished. In my experience though, these meetings make about as much sense as gathering with friends to cook one delicious, nutrition-packed meal and then counting on it to keep your body fueled and sustained for a year. You’d all starve, right? Most companies are starving from a lack of clear plans too. Let’s talk about it.

There are many pitfalls I see over and over when it comes to the annual planning cycle. Let’s dive into 3 of them, and see what can be done to turn the tide.

Pitfall 1: The goals are not actually the goals

If you are beginning the meeting with a blank sheet of paper, you have lost before you’ve started. Your plan has to be based on something. Depending on your role and the team involved, this could be any combination of the following:

The strategic goals set by your C-suite
Strategic goals and directives set by your board
Data and insights into where your business is thriving, where it is struggling, and what untapped opportunities exist (a SWOT, for example)
Regulatory changes or legislation that will impact your business

If your goals aren’t rooted in something more concrete than your wishes, I strongly suspect that by June, you will be working on a fully-new set of goals. The boss of the bosses (and data is the biggest boss of all) has to be the foundation of your goals. From there, everything else flows.

What you can do:

Get clarity from the leaders above and around you on what the Company is focused on.
Make sure your goals directly support achievement of those objectives.
Get data. Use it to inform your goal-setting.
Create a measurement for each goal and include a timeline. “Increase sales by 5% by end of June.” Not “increase awareness in the market.” I literally once heard an executive exclaim that his multi-million dollar project (which had not produced a single dollar of return), had “increased awareness around the need for this work.” What? This was at a board meeting. I am confident I did not maintain a straight face.

Note: Got a boss who doesn’t have goals? This is a tough one. Give me a call and we can work through it.

Pitfall 2: You have 4,529 goals.

I see this all the time. It is really hard making decisions. My 5-year-old struggles with it all the time and guess what? So do adults. But we must choose. We cannot realistically achieve all of the things, all of the time. In most cases 5-7 goals is the maximum number a team can manage at once. And no being sneaky and creating Russian nesting dolls of goals. A goal is a compete thing in and of itself. You can stick initiatives under it as the “how” but the goal is a singular thing. If the word “and” is in your goal, your goal is two goals. This requires a lot of discipline but it’s critical. If you took a tablespoon of peanut butter and tried to make 18 PB&Js, you’d have some unhappy children. They’d likely begin to resemble rabid pterodactyls, and you’d end up buying more peanut butter. But in the world of business, the peanut butter is human effort, and it’s not so easy to just go get more of it. Be selective and disciplined. Choose.

What can you do?

Start with the non-negotiables. You have to follow laws, even if they’re silly. You have to do what your boss says (we can argue this point, but let’s agree to it for the sake of this discussion). List these things first.
Use the data. What is going to make the biggest impact for your business as a whole? According to DATA, not the song in your heart. Add these things next.
If you are not to 7 goals yet, you get to have a little fun now. What would you like to do? Get those aspirational goals on the list.

Pitfall 3: The goals are allowed to change with the wind

Changing a goal should be like an act of Congress. Well. Maybe that’s a bad analogy right now. Changing a goal should be as difficult as getting a mad octopus into a small net. Better? The point is that there should be governance around how a goal is changed, intentional conversation about it, and a clear standing down of something in order to accommodate the new goal. Let me say that again. You can’t add a goal (please see the above reference to the peanut butter pterodactyls) without taking a goal away. And this should be a big deal that requires a lot of emails and meetings and general gnashing of teeth. Why? Because if you want your team to go hard, you can’t pull the rug out from under them without significant cost. It deflates energy. It damages trust. It hurts teams.

Now, there are some changes we can’t avoid. Laws change, boards change their minds, CEOs come and go. The point is simply that goal changing is a serious thing and should be done with care.

What you can do:

Share your goals with your leader. Share them broadly with your team. Talk about them. Make them visible.
Make noise when they are threatened by new directives that steal your team’s bandwidth.
Keep pointing to that list of agreed-upon goals. I live in the real world. I know this doesn’t always work. But TRY.

Make this a hill you may not die upon, but one on which you’d risk a few broken bones.

Pitfall 4: Wait, what did we say in January?

This is a bonus pitfall, but really the point of this blog post. You cannot hope to discuss your goals once and then go along your way successfully. The goals you set need to be visible, reviewed, often discussed, globally known (at least among your team and your boss) and tattooed on your thigh. Ok, maybe not that last one. The goals you set should form the backbone of a recurring review structure. Results should be measured. Progress should be monitored.

What you can do:

Structure your leadership meetings around review of your goals, AT LEAST quarterly. Have people bring data. Monitor progress.
Make it visible. Create a poster, a computer background, a mousepad, a billboard. It doesn’t matter how you do it but make sure the list of goals is visible. Every time a new initiative is proposed, make sure you can draw a direct line to those goals. And assess how many initiatives you already have aimed at that goal! Back to the peanut butter pterodactyls.
Focus on the red. Spend your energy on the things that are not going well. If a goal is coming along nicely, everyone clap and smile and then turn your attention to the thing that is at risk.
Assign each goal to an owner who is a member of the team that created the goals to begin with. This person is responsible for gathering data, reporting on the health of progress, advising on which initiatives will move the needle. Tip: If more than 2 goals are owned by the most senior member of the team (the boss), and that boss has a title that starts with a C, you are in dangerous territory. Proceed with caution.
Consider the role of leadership and executive coaching in keeping the team focused and on-task. Professional coaches can be an extension of the leader themself, helping to work through snags, redirecting energy, challenging departures from the plan. A leader cannot be everywhere at once. A professional coach can be an invaluable partner in maintaining forward momentum.