Strategy is not a side hustle [Article]

Strategy work requires leadership energy, capability, and personal investment from across the organization.

Too often, leaders consider participating in strategy work or strategic planning as an odd combination of an earned privilege and necessary evil – a moonlighting job compared to their ‘real work’ of delivering on revenue goals and operational metrics. There are groans and eye rolls that go along with the commencement of the annual process. These come along with prognostications about how it is just a waste of time, that the same conversations will happen in the same way with the same outcomes.

And yet, as much as people might complain about the amount of time and effort required to develop strategy, they complain even more if they are excluded from the process! Getting a seat at the strategy table is typically a sought-after form of recognition that belongs to an exclusive few and most will protect that seat at all costs.

This dichotomy creates a significant challenge for organizations trying to create strategic clarity, direction, and focus. Leaders say they want to be involved, but they view taking time to participate as a hassle or even worse, a distraction from what’s really important.

The problem with that mindset is that strategy is not a side hustle for leaders. It is a vital and integral part of senior leadership. 

If a leader’s time commitments don’t include the capacity to work on strategy with peers across the enterprise, they likely aren’t organizing their time appropriately. If the leadership team has the same conversations over and over every year and nothing really changes, the group dynamics on the team likely aren’t what they need to be. And if the approach to strategy isn’t compelling enough to inspire enthusiastic participation, they are likely using the wrong process. Let’s look at these three challenges in detail.

1. The side hustle mindset

Senior leaders often land in their roles through years of producing at high levels. They meet and exceed revenue goals, deliver exceptional operational results, and make their way into senior leadership ranks. By focusing, succeeding, and reliably delivering, leaders create a valued reputation as high producers that reinforces their beliefs about how to spend their time and energy.

As a result, leaders may feel most comfortable taking a hands-on approach to meeting metrics, working with customers, delivering on vertical results, and staying in their comfort zone – albeit with bigger budgets and more people reporting to them as they get higher in the structure. That’s both great and problematic.

When senior leaders collaborate well, enterprises grow exponentially.

In today’s increasingly interconnected and complex world, leaders must have strong enterprise-level focus, commitment, and capacity. Companies that want to grow need leaders who have a broad view of the enterprise coupled with deep vertical expertise in their specific areas. Working together on enterprise strategy is one way of gaining this level of exposure and connection. When senior leaders collaborate well, enterprises grow exponentially.

The ability to effectively engage in strategy design and planning requires leaders to create the capacity to spend time working with their peers across the enterprise. Spending time on enterprise-wide direction setting can’t be positioned as a distraction for executives who would rather be focused on their own areas.

Leaders need to see working across the enterprise as a crucial part of their ‘real jobs.’ When they do, they invest the appropriate energy in cultivating relationships with peers and building the visibility they need to participate actively and effectively in strategy work together.

2. The recycled conversation group dynamic

Strategy discussions have earned a bad reputation as being just the same conversation over and over. Those discussions are often fueled by expensive consultant-created binders of market analysis, financial forecasts, and operational recommendations. The shelf in many a CEO’s office is chock full of these strategy binders, and many of them have different logos and years but say fundamentally the same thing.

Because senior leadership teams often don’t work together regularly, they don’t have the necessary group norms to move quickly into quality conversations about where to take the company. Instead, they default to long-winded presentations in minute font size about details that the rest of the group isn’t equipped to process. And, let’s face it, most of those presentations are slanted to provide the rosiest possible report by well-meaning executives who don’t want to air their challenges to the group. It is death by PowerPoint with a side serving of obfuscation.

It takes ongoing focus and discussion about strategy to build the connective fiber needed for success.

If that sounds familiar, there are group dynamics that are preventing the team from effectively delivering and moving forward. Visible alignment to an ambitious strategy is hard to create if the strategy is only visited annually, possibly with quarterly ‘progress reports’ in between. The more complex the enterprise, the less likely it is that the group of executives who work on strategy have the relationships they need to move from agreement to alignment to deliver together. It takes ongoing focus and discussion about strategy to build the connective fiber needed for success.

3. The ineffective process factor

Many executives say that they dread their annual strategy process (and also the quarterly review processes.) They are exercises in stress – a PowerPoint pressure-cooker supplemented by Excel exhaustion. The run-up to the meetings is full of late nights preparing detailed slides and spreadsheets to be presented to people who don’t have the broader context needed to fully understand them. The time spent in actual meetings together is poorly managed and consists primarily of presentations that run too long and don’t provide a platform for quality conversations.

If we were to make a Top 5 list of things we hear most frequently about annual strategy process, this would be it:

1. The processes are boring, ineffective, take too long, and don’t drive results.
2. We say we want to be innovative but at the end of the day it is all about the numbers so why bother with all the presentations – just tell us what number to hit and we’ll go do it.
3. The meetings are frustrating because the same things get discussed and nothing changes.
4. It doesn’t really matter because everyone just goes back to their day jobs when it is over.
5. But…don’t dare exclude me (even though it sucks!)

An effective approach to setting strategy creates energy and traction across the leadership team.

Strategy discussions should be dynamic discussions of what is possible and necessary for the business. From there, building a shared understanding of the blockers and tradeoffs leaders are struggling with creates quality conversation about how to shift to deliver the strategy effectively.

Accelerate strategy, decelerate tedium

Approaching strategy as an annual chore is a legacy way of thinking about the whole idea of what a strategy is and how it helps a business to thrive. It reinforces the idea that leaders only think about enterprise strategy once a year and that the rest of the time they focus on delivering in their own areas.

For leaders to deliver together on strategy, they need to feel connected to each other and committed to the direction. That doesn’t come from dragging through long PowerPoints and tiny font Excel spreadsheets about details that don’t impact other areas.

It may seem oxymoronic, but more often takes less effort and is more productive when it comes to strategy. Our observations have been that organizations that attend to strategy throughout the year in shorter, more targeted processes (and with fewer slides) are more successful at execution and take ground far more quickly. These strategy sprints create a level of energy and connection to the strategy throughout the organization by keeping the focus at the right level for cross-organizational leadership discussion. It also keeps the strategy front of mind for everyone without distracting from the operational day-to-day plan execution that is required.

If your organization treats strategy like a side hustle for leaders, keeps having the same conversations over and over, and is using outdated processes, it is time for a complete re-imagination of strategy and how to use it as an effective tool to lead your business.

Start having the right conversations on a regular cadence about where you are collectively leading the organization and what’s getting in the way. You’ll spend less time and be more impactful over the course of a year than you will with outdated annual strategaloozas that feel painful and unproductive.