14 CEO Dilemmas

2.14.14  |  Author: Bouzha Cookman

Bouzha Cookman, Managing Partner Catlin & Cookman Group

For serial and first-time CEOs alike the job of steering a growing company is full of tough choices and conflicting demands. All agree that CEOs are responsible for marshaling products, markets, teams, customers, employees, capital and other resources to deliver profitable revenue growth.

However, regardless of experience and company stage and size, CEOs face some conundrums that may be under-appreciated.  Here are 14 ongoing CEO leadership dilemmas:

1.    Divergent Expectations

There are many, often divergent, interests of critical constituents.  It is a ceaseless task to manage the expectations and roles of co-founders, team members, employees, customers, different investors, board members, analysts, shareholders, community, and family – to name a few.

2.    Responsibility and Expectations for Employees

A weighty feeling of responsibility for employees’ livelihoods, happiness and development looms larger and larger as more and more people join the company.   However, the desire to protect jobs and create a great work environment can be tinged by extreme frustration if employees don’t appear to be as dedicated or hard working as they should be.

3.     Loyalty

No matter how necessary and how many times CEOs have done it before, demoting or shuffling loyal team members, co-founders, trusted employees is always extremely hard.  What should be done when loyalty to an individual might be preventing changes that would be better for the company?  How to manage the situation with the best results for all contituencies?

4.     Delegation

CEOs often question if they are delegating too little or too much.  The calculation usually involves a tradeoff between the cost of micro-managing, which not only takes time but can disempower employees, and taking the risk that employees might make the wrong decisions.

5.     Transparency

CEOs wonder what degree of financial transparency they should share with employees and how that transparency should evolve as companies grow.

6.     Investor Returns

CEOs always feel honor-bound to deliver the best possible outcome to their financial investors and shareholders.  Tricky situations arise when multiple shareholders have divergent liquidity horizons and different levels of future funding capacity.  How to balance short and long-term activity and planning is an ongoing challenge.  Who should be served?  Whose interests take priority over others?

7.     Growth Expectations

CEOs almost always believe their company SHOULD AND WILL GROW FASTER.  This “entrepreneurial optimism” can spill unrealistically into forecasts and commitments.  Missed expectations lead to a sense of failure and disappointment for the CEO, the employees and the investors alike.  Ironically, it is often the case that on a relative basis the company is doing well and the tone should be congratulatory instead of disturbed.

8.     Celebrating Success

They usually have such hard charging attitudes towards growth that CEOs have to be reminded to pause before attacking the next set of challenges.  They need figure out how to appropriately celebrate success.

9.     Time Allocation

What is the right balance between spending time “in the business” and spending time “on the business?”  It is so hard to avoid being sucked into fire-fighting crisis mode but dangerous if the crisis du jour continuously prevents time spentt thinking about the big picture.

10.   Comfort Zones

CEOs know that as their companies grow, they will need to extract themselves from their most recent “comfort zone” and start spending their time differently.  Discerning the new focus and figuring how to make a smooth transition is challenging.  It feels particularly uncomfortable when transitioning from a concrete “DOING” task to a more amorphous strategic leadership role.

11.  Leveraging the “Gift” of Feedback

Over time CEOs usually learn that “feedback is a gift.”   However, feedback is hard to learn how to give and receive.

12.  Being the “Final” Decision Maker

CEOs have the ultimate decsion making authority.  But there are many gray areas.  How much input should they gather?  Who should they gather input from?  Which decisions do they have to make alone? How much context should be commuicated? What if they make the 'wrong' decision? 

13.  Protecting Employees from Worry

CEOs soldier through the tough and uncertain times by working hard to appear upbeat.  They believe a big part of their job is to protect employees from potentially needless concerns.  They know that employees are always watching them for “signs.” Sometimes it is hard to mask the worry and anxiety they are really feeling.  What is the right balance between being 'positive' and being 'realistic?"

14.  Maintaining Emotional Balance

CEOs tend to fall in love with their company and/or the vision of what it can be– often right away, especially if they founded it, but almost always eventually.  It is natural to grieve when a company folds or has a hard landing, just as it is natural to be euphoric with terrific outcomes.  The dilemma is how to best balance passion, commitment and optimism with objectivity and realism to keep the emotional rollercoaster under control.


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