10 Ways to Ensure Your Strategy Session Fails
The Most Likely Ways That Executive Strategy Sessions Fail
Somehow you coordinated five different executive schedules to find a block of time for the quarterly strategy session. Those hours will determine the future of your business-
how you will adapt your business strategy to changing market conditions
what new goals to set for the team
who to hire to reach those new goals
-and the impact of those decisions cannot be understated. This strategy session cannot afford to fail.
Here’s How You Will Fail
Failure #1: Invite The Wrong People
An effective strategy session needs to include the people who are most critical to the decision-making process. For most businesses, that will include the CEO and other C-suite leaders. However, it’s difficult to draw the line between who should be in the room and who will be outside the room, especially at small organizations. Weak leadership teams would rather attempt to be inclusive and allow entry-level staff to participate than exclude a well-loved but irrelevant staff member.
An impact of having the wrong people in the room is that decisions focus on fringe issues and making accommodations, rather than a clear and simple plan for the biggest and most important issues.
Failure #2: Invite Too Many People
An effective strategy session should balance idea generation with idea prioritization. Bringing in multiple perspectives helps generate ideas, however every additional person provides friction when decisions need to be made. Similar to “The Wrong People” problem, leadership teams that default to inclusivity are tempted to involve too many individuals during the prioritization phase and add too much friction. This makes consensus difficult and can result in the popular-and-fun ideas taking precedence over the boring-but business critical- strategies.
For both #1 and #2, tough decisions around the RSVP list should be made based on the ultimate goal or compelling question for the strategy session…
Failure #3: No Goal Or Compelling Question
Sound strategies need context. Before kicking off a strategy session, a business needs to recognize the challenges they are facing today and likely to face tomorrow to provide a frame of reference for what a useful strategy should accomplish. Without a focus or frame, strategy sessions can devolve into pursuing pet projects or ego-driven goals.
Effective strategy sessions have either a goal they are trying to achieve (“Generate a new talent strategy”) or a compelling question to define what’s important (“How can we be positioned to be an employer of choice in the upcoming year?”).
This frame of reference makes it much easier to decide who should be in the room: if the goal/question hinges on talent, HR should definitely be there, whereas if the goal/question is about go-to-market strategy, the Chief Sales Officer should be first on the list.
Failure #4: Don't Consider The Tactical Execution And Overestimate Your Organization’s Ability To Execute
A strategy session is most likely to fail the minute the strategy conversation ends and the tactical conversation begins:
These and many more quagmires await a leadership team trotting out their new sparkling strategy after a well-run executive offsite.
There isn’t a simple hack that can anticipate the many challenges that crop up when a strategy needs to be enacted. However, building strong feedback loops into any strategic plan can help a leadership team calibrate once things have started going sideways. Surveying staff and customers, building in multiple checkpoints with the teams that are the most impacted by change, and being prepared with a Plan B and Plan C are all ways to mitigate unexpected problems.
Failure #5: Make Sure The Most Important Attendee Has The First Word, The Last Word, And The Most Words In Between
Executive presence is a sharp sword that can be easily abused. When the individual with the most power or status contributes to a strategic discussion, it’s easy for their opinions to count more or be seen more favorably than someone with less status. This can chill a room, silence participants, and promote a culture of simply going along with whatever the CEO says. This gets even more lopsided when gender and age influence the status disparity.
To prevent this problem, a CEO should self-regulate by contributing only when necessary, focus on asking questions rather than answering them, and elevating others’ voices. A strategy session can also be designed in a way that allows space for all participants to contribute, vote, or debate: Post-It notes can help anonymize idea contribution, vote-by-stickers can anonymize prioritization, and round-robin discussions can ensure every participant is heard.
Failure #6: Only Say Yes. Only Say No. Only Say Maybe.
Strategic choices often have to be made on imperfect information. It’s easy to slip into rhythm where making a firm Yes or No feels risky or impossible. What this leads to is that every decision is consistently met with one of three responses:
Too optimistic: “Anything is possible, so let’s say yes to everything”
Too pessimistic: “We cannot make any choices because we don’t have enough of/all the facts”
Too indecisive: “That could work but it also could not work: let’s add it to the pool of options to decide on later”
A facilitator greatly helps in pushing strategy session participants to make a decision and move discussions forward. Without a facilitator, a strategic team needs a constraint such as, “We need to have picked one- and only one!- strategy at the end of this session in order to have the time to effectively execute before year end.”
Failure #7: Do Everything During The Session
Not every leader comes to conclusions in the same manner. Some people are quick to think on their feet, whereas others like to process through options to identify the best choice. Neither approach is necessarily better or worse, but often strategy sessions are designed around the fast thinkers versus the slow processors.
The biggest culprits are leaders that like a dramatic reveal. A strategy session that unveils critical information during the session and asks participants to think out loud puts slow processors at a disadvantage. This then prevents slow processors’ best ideas from being included because they were not given the opportunity to participate in a way that allows them to do their best work.
A simple fix is to share all data, reports, and target outcomes in advance. Transparency around the goal/compelling question is also critical to share in advance so slow processors can prepare.
Failure #8: Only Entertain Realistic Ideas
Change happens in multiple ways: it can be slow and gradual, it can be exponential, it can be punctuated equilibrium, and more. A strategy session is a chance to detach from the present day to forecast how an organization will best handle change, however a focus on “realistic” ideas will only address certain kinds of change.
A leadership team that deals in only realistic ideas is at risk of being backwards-focused than future-focused. Paradigm shifts such as a new disruptive technology, a new competitor, or a macro-economic shift (such as COVID-19) catch backwards-looking teams off-guard. Those large-scale changes often require innovation to solve and may require you to throw out the playbook of how your organization has solved problems in the past.
Every strategy session with a clear goal or compelling question should include an idea generation phase that does not dismiss unrealistic ideas. A piece of an unrealistic idea may solve an impending problem better than a fully-realistic idea!
Failure #9: Expect Everyone To Produce Work During The Strategy Session
Two major pitfalls happen when a leader has to produce work results while also attending an extended strategy session:
Participants can’t fully focus because they are managing day-to-day issues while in the strategy session
Regularly over-demanding leadership attention can lead to leader burnout
Preparing for an extended strategy session (such as a two-day annual executive offsite) happens months in advance to prepare middle management and front-line staff to perform independently. This can look like generating standard operating procedures, defining escalation avenues, and vesting decision-making power to middle managers during the duration of the offsite.
Properly providing the breathing room for leaders to disconnect from day-to-day work will lead to better long-term outcomes while building internal resiliency.
Failure #10: Plan, Facilitate, And Participate In Everything
When a leader owns every stage of the process and is a participant in the process, it can lead to participants feeling as though they don’t really matter. This manifests in participants that don’t feel welcome to contribute, feel disincentivized to disagree, and won’t faithfully execute the session’s outcome. It is as if a parent decided everything for a teenager’s birthday and only allowed them to blow out the candles.
Beyond making it difficult for participants to buy into the strategy session, splitting attention between the planning, facilitating, and contributing responsibilities does not set anyone up for success. It’s hard to know when to contribute, while being sensitive to contributing too much, while also driving the conversation forward to stay on schedule…it’s a lot!
Involving participants in the design process by assigning them ownership can help generate buy-in on the process. Hiring a facilitator can also lessen the load on the organizer from managing the conversation to being a part of it.
How Else Will You Fail?
Is there something we missed? Let us know how you’ve seen strategy sessions fail in the comments.
