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The Benefits of Generalist Leadership and How to Cultivate It

At the start of January, the digital landscape is littered with articles about leadership trends and best practices in the new year. Despite the framing of their missives, most of them boil down to evergreen questions. 

Why and how do leaders succeed? How do they continue to grow and improve? What are the differences between leading a small organization and a large one? 

All of these questions matter. Many argue that answers specific to a specialization yield the most valuable insights. That’s an understandable position. No one wants to be the proverbial, “jack of all trades, master of none.”

But perhaps that assumption answers the wrong question: is specialization really the best approach to leadership in the first place?

The Value of Generalist Leadership

I’ve been reading David Epstein’s excellent book Range: Why Generalists Triumph in a Specialized World. As the title suggests, it goes against conventional wisdom regarding the value of specialization. Generalists, he argues, are better poised for success. 

Thinking about these arguments in the context of elevating emerging leaders within our organizations, I found it increasingly difficult to argue with Epstein’s premise.

The business world seems to agree. A 10-year Harvard Business Review study of 17,000 C-Suite executives found that 90% came into the role with generalist experience

The top of the organization seems to belong to the exceedingly well-rounded leader with expertise in as many areas of the business as possible. How do we build more of them?

Encourage Expansive Learning to Develop Talent

Nurturing talent within an organization improves its odds of success. Open, honest communication improves our understanding of how people want to grow under our roof, but that’s only one piece of the puzzle.

The bigger challenge is finding out how we help them grow. On that note, you’ll find no shortage of articles telling you that companies and employees should invest in professional development that deepens specialization. 

But perhaps the better approach is to train them in more than one part of the business. There is an argument to be made that understanding how different pieces of the company work together improves an employee’s work in their own specialty and promotes broader strategic thinking. 

Ideally, this takes place in-house. In some cases, though, employers may still benefit from an individual leaving the organization entirely. If an employee gathers varied experience at another company and comes back with what they’ve learned, they may provide value that internal cross-functional training couldn’t have generated.

Pay Attention to Shifting Sentiment in Growing Leaders

A while back, a fellow that I’ve been mentoring was offered a job at another company and was getting ready to leave his own. When he told his employer that he was leaving, they said, “Oh, really? Why?”

As it turned out, he had been about to receive a significant raise and more responsibility! 

Needless to say, he accepted the bigger raise, more responsibility, and better title. I’m happy for him and for his employer.

This event speaks to why it’s important for employers hoping to build (and retain) budding leaders should keep their finger on the pulse of employee job satisfaction. An approach of “managing by wandering around” may enable leaders and their teams to see and think more about the big picture.

Keep Your “Head Up”

“Heads Up Management” refers to working on the business instead of just working in the business. When you have your head down and are buried in your own work, there’s very little you can see. Looking up broadens and informs a more comprehensive perspective. You can see other people with their unique viewpoints. You can see the bigger picture of where your people fit into the business. 

In addition to reinforcing a generalist perspective in existing leadership, it enables the company to foster future generalist leaders. For example, people might come into a traditional entry-level role and stay there for somewhere between five months and a year. Over the first two years in the business, they might be moved through several different business units. All the while, they are being evaluated and determining where they’d like to go with the organization and how. 

Heads Up Management gives you the bird’s eye view needed to parse employee contributions and see where adjustments might be made to continue future leader growth.

Use a “Long-Term” Approach to Growing Leaders

One of the Four Questions we often ask at our firm is, “How do you define long-term?” 

In the context of developing generalist leaders, the long-term should focus on employee progression beyond responsibility for limited and specific tasks. That often includes managing other people doing those same tasks and others.

Encouraging the development of generalist thinking may improve employee success along this long-term path. Giving people the opportunity to witness other parts of the organization in action can model the importance of such perspectives, building future leaders of a stronger organization.

The Role of Generalist Leadership in Small Businesses

It’s possible that you’ve read this advice and thought, “That won’t work for my business. We’re just too small.”

This is the wrong way to think about it. You might be surprised by the value derived from exploring the distinctive experiences your small team brings to the table. And approaches like Heads Up Management may help you identify opportunities to look to people outside your organization to fill in skill gaps.

Does generalist leadership development work with around 25 people? Are there generalist growth and mobility opportunities for ourselves and those around us? Can we encourage and nurture greater range in such an environment?

In a word: yes.

Embrace Organizational Overlap to Elevate Generalist Development

You may be surprised to learn that there may be even more talent and experience diversity in smaller organizations than in larger ones. 

In certain large companies, your peers usually have a very similar set of skills and experiences to what you already have by the time you reach a leadership role. In a smaller organization, you usually have peers from all different types of backgrounds collaborating, each with their own lived experiences and perspectives. 

Emphasize Cross-Functional Training

The development of generalist leadership in a smaller organization may be even more important than in larger ones. There are likely not going to be as many peers an employee can turn to and say, “I’m experiencing this. What do you think about it? How has your experience been similar or different?” 

Fortunately, the very nature of growing and managing a small business fosters generalist leadership. There’s a lot to do and not enough hours in a day, so people end up wearing multiple hats. As a result, employees often gain exposure to a broader range of capability sets by default. 

Baked-in generalist development at a small business is a good starting point, of course. But companies that want to make sure the mentality continues as they scale need to make it a deliberate choice.  Ensuring you have the capability to continue providing opportunities for exposure to other people and departments for the sake of diverse learning sets you up for ongoing success. 

It’s Time to Blow Up the Silos

If a person is going to become a true leader at some point in their career, it’s going to be far more challenging if they only understand one piece of the company. Even a small business may benefit from breaking down silos. 

Having a variety of experiences like the kind described in Range helps both current and emerging leaders alike. The business’s long-term profitability and culture will benefit for years to come as a result.

It is said that variety is the spice of life. It might also be the secret ingredient in developing effective leaders.  

Developing strong leaders is critical to growing any company, but that’s just one piece of the HR puzzle. Our on-demand webinars can help you understand the big picture. These include:

For more information about our on-demand webinar series, click here.

This is an updated version of an article from April 2020. ©2023. DailyDACTM, LLC d/b/a/ Financial PoiseTM. This article is subject to the disclaimers found here.


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About David Spitulnik

David Spitulnik is a successful executive with over 40 years of experience in both large technology companies and in consulting to and leadership of mid-market, closely held and family owned businesses across a variety of industries. In addition to serving as chair of the Private Directors Association’s Private and Family Business Center Outreach Committee, David…

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