Conquering uncertainty as a Chief of Staff

September 15, 20216 min read
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The most difficult challenges we face aren’t overbearing leaders or tough competition. They are the ones we create for ourselves.

Challenges have been plentiful in my time as a Chief of Staff. Organizational challenges, defining my role , and more. None have been more difficult than imposter syndrome. Imposter syndrome is a self-defeating belief that makes you feel like a fraud, especially in a professional context.

You don’t feel good enough. You doubt your abilities, talents, and accomplishments constantly. Been there? We all have.

The root cause is  uncertainty . Uncertainty with: 

  1. If you’re doing the right things
  2. If you’re doing the right things in the right way
  3. If you’re doing the right things in the right way at the right time.   

As a Chief of Staff, you can face this uncertainty because of general, vague mandates. Where problems persist, communities exist — the number of online communities focused on connecting and creating discussions amongst Chiefs of Staff has exploded in the last year. These communities allow us to connect on a deeper level and ask each other tough questions to gain a higher level of clarity. 

Clarity comes through our process of benchmarking, or personally, gaining understanding through comparison:

  • If the success I’m achieving is similar to others
  • If the struggles I or my organization is facing compare to others
  • If the questions I have about my role, career, or outlook are shared amongst others.  

With all of these “ifs” (six to be exact), our goal is clear — strengthen mission clarity for the Chief of Staff.

We partnered with Prime Chief of Staff to create a benchmark supporting this goal. Where does the Chief of Staff role stand among leadership? How has the role has evolved? How do Chiefs of Staff feel about their organizations, themselves, and their most thought-about topics?

These insights point to one recurring idea — Chiefs of Staff are becoming the point guard for organizations. Let’s explore four major insights from  this report  that support this idea. 

Insight 1: Strategy is king  

In basketball, the point guard can score (execute) but focuses on seeing the visual flow of the game (strategy) and assisting other players’ strengths (amplification). 

Two data points in the report frame contrasting attachments to strategy in the Chief of Staff role — importance versus pertinence. 93% of Chiefs of Staff believe they have an important role in communicating strategy; 89% believe their roles are important for creating and executing strategy.

However, the extent to which they feel critically important to strategy is not as high as one would think. Only 57% strongly agree that their role is important in ‘developing’ strategic priorities.

Is the Chief of Staff cut out to be the point guard if there is no urgency to fill that role? 

The data suggests a sense of urgency around strategy, but this urgency is rooted beyond the Chief of Staff. Over the last year, 61% of businesses stated they are spending more time on strategic planning. 

Post pandemic, the Chief of Staff role has paralleled strategy’s growth in importance (81% believe the position is “more important”). Where (and why) does the Chief of Staff come into the strategy picture? 

Dealing with variability is the point of impact. While Chiefs of Staff may not be a critical piece in defining or setting strategy (a responsibility on the shoulders of the CEO and CSO), they are crucial in making sure the “trains run on time” and ensuring the business is effective in executing the strategy.

In basketball, a point guard’s ability to transition and adapt to the defense is crucial for the offense’s success. Strategy variability is the ultimate tell of success for point guards and Chiefs of Staff.

Insight 2: Chief of Staff is the new CEO (Chief Execution Officer) 

Executing a strategy is like lobbing the basketball towards the backboard. It might go in, it might not.

Executing a strategy effectively is aiming for the hoop with textbook form and an open shot.

Effective strategy execution requires cross-functionality from top to bottom, side to side. Like a point guard, you have to work with your forwards (managers), the other guards (leaders), and your center (workforce) to make the offense flow.

For organizations, more impactful point guards = winning games (business). 

As the significance of the Chief of Staff has increased, 74% of organizations feel as though they are effectively executing and communicating cross-functional initiatives. 

Managing these initiatives, like maintaining a winning streak, isn’t always glorious. Competing priorities, lack of resources, and disruption of ‘business as usual’ all come into play — like teammate egos, a slacking bench, and players being unwilling to push themselves.

These are all risks that the Chief of Staff (point guard) is there to reduce. 

Insight 3: Chiefs of Staff need their own stack 

Supporting proper strategy execution management requires more than blind faith.

As point guards need specific skill drills, workout routines, and world-class nutrition, Chiefs of Staff need all the support they can get too. Today’s world of hybrid workforces, competing time zones, and operational flexibility demands technology as a massive piece of the puzzle.

Unfortunately, only 1 in 4 Chiefs of Staff feels that they have the right technology in place to benefit their role. Knee jerk question: if Chiefs of Staff are horizontal as a leader, isn’t every piece of technology — from CRM to Product Analytics — supporting them? Yes and no.

Chiefs of Staff rely on the outcomes of what the organization is producing. Those outcomes are regularly translated into data points or results in different tools. Aggregating those data points for the Chief of Staff to have a comprehensive and consistent story is key. 

Point guards can practice and work out all they want. Until they play a game and look at their stat line, they don’t know how to gauge their performance or if they can execute when the game is on the line.

Chiefs of Staff need this too — a collection of outcomes in one place that integrates with all of the technology across an organization. Without this place, the Chief of Staff will find themselves searching and reacting rather than consulting and proactively executing.

Insight 4: The Chief of Staff evolution brings excitement and uncertainty 

The Chief of Staff role has been heralded as an exciting position in many companies, paralleling how point guards inspire some of the best offenses in pro basketball. 

Chiefs of Staff engage with executives. Point guards lead the charge on the court. Managing cross-functional initiatives and communicating with investors is the Chief of Staff’s game, just as point guards direct their teammates and construct offensive gameplans. When it comes to game-changing decisions, the Chief of Staff and point guard feel in control.

The role has evolved year over year, leading to Chiefs of Staff self-questioning and comparing their responsibilities to others. Compensation, CoS success metrics, and support from a professional point of view are a few that respondents request to be covered in the future, becoming hot topic discussions in Chief of Staff communities. 

The Future of the Chief of Staff  

The insights are clear: the Chief of Staff role has greater significance than ever in organization, but a long way to go before evolving into an unambiguous role. Strategy and execution are top of mind for all Chiefs of Staff — the transition of this mindset is beginning to bear fruit.

Organizations have an opportunity to support their strategy-execution management via the development of their own Chief of Staff, as basketball coaches have the opportunity to develop their bench players to become future starters. The Chief of Staff has the opportunity to blossom into a full-blown organizational point guard, with pinpoint precision and playmaking abilities like Steph Curry.

While everyone seems to be hiring for a Chief of Staff, not all positions are created equal. Gaining clarity of the Chief of Staff‘s involvement in strategy execution management, and how supportive their principals are, is key to the role’s success.

Ready to take the next step in finding greater purpose in your role?  Download our free whitepaper, Driving Organizational Effectiveness as a Chief of Staff.