5 Common Dilemmas for Today's Leaders

As the CEO of a growing company, you understand that your role is predominantly about staying true to – and developing – the vision you and your leadership team have for the business.

This is an exciting responsibility to undertake, but you may also be aware of how complicated it is to achieve in practice. The day-to-day minutiae of your role reveal that, in reality, it is about balancing the seemingly competing priorities of all sides of the business.

The good news is that you’re not alone. In fact, a McKinsey study of 100 senior leaders shows that there are five dilemmas faced by today’s CEOs. [1] These are:

1. Preserving the core vs. innovating for the future.
2. Delivering short-term results vs. investing in long-term performance.
3. Managing a team of individual stars vs. maximizing a star team.
4. Empowering the team vs. maintaining sole control.
5. Immersing fully in the role of CEO vs. retaining personal identity.

In this article, we look at how CEOs can handle these common challenges.

Dealing With the Five Common Dilemmas

First, you need to recognize that you are a leader, not a superhero. There may be a tendency in modern society – and even within your own team – to place CEOs on a pedestal. But it helps to bear in mind that you'll probably face the same fears and insecurities as everyone else.

So, don’t dismiss these experiences as weaknesses. In fact, being able to observe and maturely process emotions is one of the standout traits of high-performing leaders.

Second, although we present these dilemmas as distinctions between two possibilities, they're not mutually exclusive options. In other words, the idea is to bring unity to what at first might seem like competing ideas. As you’ll see, this is where your leadership skills will really come into play.

Let’s take a look at the five dilemmas one at a time.

1. Preserving the Core vs. Innovating for the Future

In his book "Start With Why," Simon Sinek discusses at length the fate that befell much of America’s railroad industry in the wake of commercial air travel.

The central thrust of his argument is that to avoid fading into obscurity, companies must reconnect with their purpose (their why) and innovate what they do in order to stay relevant. If those companies had pivoted to air travel, they may well have survived.

Clearly, this an even greater challenge for today’s CEOs, as the pace of technology continues to quicken.

But this issue is particularly acute in companies that have been in the same hands for multiple generations. In this situation, one of the biggest hurdles is likely going to be to persuade the owners to buy into the necessary changes. Resolving such problems requires a delicate process of listening to senior stakeholders and transforming the company vision to make it fit for the future.

But it’s possible to develop a modern customer-centric and data-driven approach to business, whilst retaining the traditional values that underpin the traditional organization in the first place.

2. Delivering Short-Term Results vs. Investing in Long-Term Performance

As CEO, you’ll probably know how tempting it can be to seek short-term results. You’ll have also probably felt the anxiety that can come from trusting in your longer-term goals.

Investing in the long-term is indeed a trust exercise, as noted by Steve Jobs when he said, “You can't connect the dots looking forward; you can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future.” [2] This can be a tricky one to balance for even the most experienced CEOs.

But short-term and long-term need not necessarily compete. In fact, they can be complementary. CEOs need to have a portfolio of projects, some which deliver short-term results, and others which deliver in the longer term.

The key factor is clear communication with stakeholders. Keep everyone in the loop and on board, regardless of the project timeframe.

3. Managing a Team of Individual Stars vs. Maximizing a Star Team

It might be generally true that in business, the whole is greater than the sum of its parts, but as CEO you'll recognize how advantageous it can be to have star players.

Problems can arise, however, when high performers don’t integrate with the wider team. They may well deliver exceptional results, but, in the long run, this can create deeper problems within the organization.

One of the core characteristics of a star team is cohesion, drawing on a delicate balance of shared values and a willingness to pull in the same direction. As CEO you may need to consider letting go anyone who severely compromises cultural cohesion.

By all means, nurture your standout players, but not at the expense of your corporate values.

4. Empowering the Team to Make Critical Decisions vs. Maintaining Sole Control of Outcomes

As CEO, you know that the buck stops with you. But as you’ll also know, that doesn’t mean you need to have your hands on the steering wheel of every role within your organization. Delegation is a vital skill to integrate, but how do you know when and what to let go of, and to whom?

It is fair to say that the skill of delegation tends to come with experience, and so may be trickier for newer CEOs. But even experienced CEOs admit that they still have trouble stepping back if they’re concerned that their teams might make mistakes. They likely end up staying late in the office to check detailed reports for errors.

But as with the previous dilemma on short- vs. long-term thinking, trust plays its part. There’s a distinction between so-called “gofer” delegation and stewardship delegation. The former rests more on instruction and fixed process: the latter allows for greater intuition and leadership by the delegate.

As CEO, you need to address this challenge mindfully, and with a degree of acceptance that each situation calls for a tailored approach.

5. Immersing Fully in the Role of CEO vs. Retaining Personal Identity and Sense of Purpose

As an engaged and passionate CEO, it can be easy to allow business to take over your life. And as the business and team grows, the demands on your time and energy can also expand.

However, as the saying goes, you cannot pour from an empty cup. So, it's important to think of ways in which you can rest, as well as enjoy other areas of your life.

Many CEOs express the importance of staying “in the moment,” engaging 100 percent in whatever they are doing, inside and outside the workplace.

The CEOs who can strike a positive balance between their role as leader and being engaged in other areas of life often have one thing in common: a strong sense of purpose.

Clarity of mission may actually help integrate the whole person, meaning that the distinction between CEO and personal identity might actually be complementary, rather than contrasting.

Frequently Asked Questions

Q: How can CEOs balance preserving core values with innovation?

Leaders should aim to retain their organization’s core values while embracing modern, customer-centric strategies to stay relevant in fast-changing markets, aligning both tradition and future growth.

Q: How should CEOs approach short-term vs. long-term decision making?

CEOs should pursue a mix of projects delivering both short- and long-term results, ensuring clear communication with stakeholders to maintain trust in the company’s future direction.

Q: What is the best way to manage high-performing individuals within a team?

While nurturing individual stars, CEOs must prioritize team cohesion, ensuring that no single individual undermines the organization’s shared values and collaborative culture.

Q: How can CEOs maintain a healthy balance between their work and personal identity?

Leaders can stay engaged by cultivating a strong sense of purpose, integrating their personal and professional lives, and ensuring they rest and enjoy life beyond work.