Strategy Season: Why Strategies Fail

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I’ve sat through at least a dozen internal team strategy meetings. At first, as a fly on the wall and meeting organizer. I was there to make sure the coffee was brewed and the bagels were sliced. But later, I had a seat at the table and was an active participant in the creation of annual and longer-term strategies. I even facilitated some of these sessions.

So, it shouldn’t be surprising that I’ve learned a few things over the years. And no, I don’t mean making sure there’s always a fresh pot of coffee brewing (although, that is a good tip!). Take it from someone who has sat in your chair, strategy development is hard and executing the strategy can be almost impossible if conditions aren’t “right”. To help, I’ve compiled a list of what not to do this Strategy Season.


5 Reasons why Strategies Fail

I’ve experienced the elation of hitting goals, surpassing projects, and the other benefits of executing a quality strategy to a T. I also know how disheartening it is when things don’t go to plan. Sometimes, it’s gotten down to the wire and we’re finding out in January if the strategy was successful for the prior year. Other times, we’ve known by June that it likely won’t work unless we all roll up our sleeves and dig in—working harder and longer in an effort to “make it work”. And that, quite frankly, is a topic for another blog post entirely.

So why don’t strategies work? What causes them to sputter out, lose their shininess and, well… fail? Here’s a breakdown of the five major mistakes I’ve witnessed teams and leaders make during strategy season that have directly impacted their ability to reach business goals.


Lack of owner or executive involvement

Years ago, I was part of a leadership team that operated separately from the organization’s owner. Our role was to represent our teams as department heads and work together to develop strategies and campaigns to grow the business. The owner was kept in the loop of these plans and had final approval, but was not involved in their creation.

As you may imagine, without the owner involved in the process there was confusion over priorities, bandwidth and even budget (to name a few). The leadership team ideated for hours and came up with great ideas, many of which never got off the ground because no one but the department head was passionate about them. Without executive involvement, it’s extremely difficult to get executive buy-in. Further, the business owner can be extremely helpful in getting organizational buy-in when it comes time for the big reveal.


team dysfunction

What happens when you put a group of people around the strategy table who don’t get along with each other? Worse yet, what happens when some of those people don’t trust and listen to others? Frankly, a whole lot of nothing.

In the example I shared above, I didn’t mention the team of leaders who met without the owner had some real dysfunction going on. I can identify several from the cast of characters Mike Elliott shared in his recent article on team dysfunction. As a result of this, the strategy was approved by most team members but not all. And, by the end of the strategy retreat, we all needed a vacation. We were already burned out from work we hadn’t even started yet. Which, unfortunately, was felt by all team members when we returned to the office for the big reveal. There was no excitement. No questions. Everyone could feel the conflict radiating from the organizational leaders. Which leads me to my next reason why strategies fail.


Strategy by best seller

Our team isn’t working well together, so let’s read a book about teamwork and model our strategy session on it. Sound familiar? What made this approach fail was that we didn’t bring in an outside expert trained on the approach to guide our session so we didn’t devolve back into bad habits.

The results? We all read a book that is now collecting dust. There may have been a bit of self-awareness realized but nothing changed within team dynamics. By June, all new processes created to support the strategy had been long forgotten.


uneven representation or Participation

Just because all of the leaders are at the table doesn’t mean every employee is represented. And, even leaders who are at the table may not be fully engaged thanks to others who talk more than listen and session facilitators who rationalize a lack of participation as a sign of acceptance or agreement.

I found this happened often when I worked in technology and many of the folks developing the software were more introverted, thoughtful and less likely to spitball or ideate without having all of the information in front of them. Can you guess what happens when sales and marketing teams develop a strategy for a software company without the developers’ insights and approval?


lack of clarity

And, finally, a lack of clarity. Successful strategies are specific and clear. Clear on goals, roles, tactics, requirements, processes, etc. They don’t require translating.

“It is impossible to improve your performance without strategic clarity.” – Ann Latham (Forbes)


Everyone within the organization should be able to see how they impact the likelihood of a successful strategy execution. Not to mention, the why! Why are we even doing this? (Hint: To make more money isn’t the answer here. Dig deeper.)


This Strategy Season, I challenge you—regardless of your role in the room—to avoid the above reasons why strategies fail by staying engaged, curious, and intentional. Ask questions to dig deeper, gain clarity and hear new perspectives. Challenge team members without attacking them. Read books that genuinely interest you for insights and to generate ideas. And, be honest with yourself and fellow strategy participants. Leave your ego at the door. Your organization’s success may just depend on it.



Ready for more content on Strategy Season? You’ll enjoy this read from Leadership Consultant Mandy Haskett on making a people strategy part of your business strategy.

And, don’t miss “Re-boarding Your Employees” by ADVISA’s President, Heather Haas.