For those who like to skim, this article will address What’s going on, What this looks like, and 3 ways leaders can address follow any of the links here to skip ahead.

People who end up as first don’t actually set out to be first. They set out to do something they love

Condoleezza Rice

What’s going on

In the early stages of an idea, movement, or organization, a willingness to do whatever it takes, often rapidly taking on a plethora of tasks they know little about, is not only commendable, but necessary. However, as such efforts take root, there are only so many details one can physically attend to, doing everything becomes a “jack of all trades master of none”, moving at the speed of light just means moving so fast no one else can keep up.

You can start to see when these traits go from blessing to curses when stagnant growth shows up, devout stakeholders quietly start leaving, or, and as we are seeing very commonly, the pioneer flames out often taking their personal lives (health, family, etc.) and the work they put so much of their blood sweat and tears with them. Just to put this in perspective, a recent study by Entrepreneur found that over half, 53% of entrepreneurs suffered burnout in the last year¹. That burnout likely contributes significantly to the estimated $300 billion annually that burnout costs the US².

What this looks like

It was hard to tell as day turned into night through the one semi-opaque window in the modest office of once such pioneer. Despite the simple set up in the aging building, to call this man “larger than life” would be an understatement. 15 years earlier he and his family took extraordinary risk giving up steady paying work, leveraging all of their long-term savings, and entering into a market that everyone thought was unattainable. 

Nevertheless, whether it was by incredible vision, sheer grit, or a combination of both, he had done it. Together with a ragtag group of followers, they built what had now become a few-hundred-person organization and growing…well, kind of. On this particular night he was sitting with a consultant, who, while just as impressed as many with his success, after spending significant time observing the organization and conducting numerous interviews with some of his most faithful team members, had identified some quickly festering issues that were growing as the organization grew. If they remained unaddressed, that organizational growth would turn into shrinking.

Revelation

Their conversation that evening was somewhat of a dance to get to an approach to discuss the core issues while respecting the tremendous work this founder had accomplished.

“I see the issue; you’re doing all this yourself.” The consultant’s statement seemed be the breakthrough moment in the conversation. Some of the issues plaguing the organization where as follows.

• Opaque glass ceilings – The ragtag team, wasn’t ragtag anymore. They had matured and were just as hard-working as their founder, yet their growth remained stunted by lack of opportunity. Additionally, discussions with folks found both growing concern and hurt as these highly-dedicated people felt disempowered to act preemptively on actions they knew would be problematic.
• It’s all in his head – There was very little documentation of processes, definition of roles, or clear communication causing heavy reliance on the founder to provide this and consequently they struggled when he was not there. Newer team members and patrons received mixed messages as the founder and team members relied on information limited to personal relationships. Often knee-jerk changes were required once the correct or fuller information entered the picture.
• Struggling to find a place – People started leaving, patrons were slowly starting to question if they had a place, and those who hung on knew there needed to be drastic changes if the good work they started was going to endure. Everyone knew and admired the founder’s place, but were increasingly questioning their own…or if they even had one at all

Seeing beyond yesterday’s success

The statement by the consultant was a breakthrough, because it was true. At the root of all these issues, the founder himself had become a bottleneck and the organization was suffering. Due to the founder’s remarkable reputation, few saw past to the core and those on the inside who did see it did not have an avenue to raise the issue to their leader.

However, once the topic had been breached, the floodgates opened. With the support of an outside consultancy, the organization began a multi-year leadership reformation.

• Raising the roof – A fit gap was developed creating a vision for what their organization should look like and a path for getting them there, including restructuring their oversite boards. Roles for supporting senior leaders were created. Not only was the pioneer no longer alone, the leadership had strategically begun to elevate the most critical voices needed to take the organization forward.
• Getting it on paper – As leadership at the highest level moved in to place, the process of documenting job descriptions and processes including adopting new tech had begun. As information became more accessible, so did the ability to clarify and address problems accurately, drive alignment, and most importantly alleviate bottlenecks, including that of the pioneer himself.
• Creating a place – With increased leadership capacity generated by both the engagement of senior leaders and the efficiencies gained through documentation and automation, attention was able to turn to the broader organization. Younger leaders, with room to grow, were developed to help shoulder the load and properly serve both team members and patrons.

Explosive growth

The result, the organization doubled in 5 years, was tripled in less than 10. Not only did much of the original team receive opportunities for increased growth, but there opened many roles that had never existed before. But the change was not just internal. The unity, clarity, and security created by a strengthened and activated leadership team gave them credibility with lenders, the community, and partner organizations.

They were able to replace the aging building that not only gave a place for existing patrons, but welcomed the steadily growing numbers of new ones. Struggling partners merged with the organization bringing a slew of additional talent and expanding to several additional locations.  As for the founder, the man who once did just about everything, is able to watch as the team he developed takes his vision to a place he never could have on his own and that will long succeed him…and take a vacation without worry.

How leaders can address…and Nikkiforos can help

1.      Prioritize the work that truly demands the pioneer’s time

While there is so much to say about the need to take care of the home folks (i.e. your family and health), setting boundaries, and learning to rest (after all, even God rested), there are many, many articles out there addressing these issues. However, properly heeding this advice must go beyond taking a vacation, proper processes, structures, and people within your organization must be set up to be truly successful starting with a process for identifying what truly “needs” to be done by a pioneer and not only what can be done by others, but what “should” be done others.

• Work that that can be done for a lower cost. For example, if a pioneer’s hourly rate is $100 an hour, they should not be mowing the lawn that can be done for $15.
• Tasks requiring advanced expertise outside of the pioneer’s core wheelhouse. For example, just because one may have a finance degree and are able to do one’s own taxes.  If one must to file taxes in 4 of the highest taxed states requiring days of work, paying someone who does taxes day in and day out with fancy advanced software is worth their price.
• Established ways of working in your organization should have a plan for developing in others to ensure a pipeline of talent over time. While it may be more efficient for a more experienced leader to do the task, failure to take the time to develop talent who can serve as backups, succession, and provide overall opportunity within the organization can threaten its long-term viability. See our post Trend #2 – Burnout and Boredom for more.

2.      Setup the structures to facilitate success,

Items such as clear org charts, role definitions, and IT design are paramount to successful, sustainable growth. Often times so much is in the pioneer’s head which makes supporting the pioneer even more difficult. Additionally, the early adopters of a pioneer’s work will often take on the “do it all” mindset resulting in either duplicate work or a “if everyone is doing it, no one is” problem. 

As such, it is imperative to clarify reporting structures, how work is organized, and the expectations of the roles tasked with completing them. Limited IT access bottlenecks work to specific individuals. Confusion on task ownership ends up in errors/inconsistencies on execution. Workers receiving direction from multiple leaders end up in a “serving 2 masters” situation driving frustration and headaches for all.  No matter of personal boundaries can overcome structural hurdles that will suck the pioneer back in to the detriment of all.

3.      Teach pioneers to delegate and manage systems.

 2 key points immediately come to mind when discussing delegation:

• the pioneer’s concern that there is no one to delegate to, and
• the caution that delegation is not dumping.

Commonly, by the time a pioneer realizes he/she must delegate, it is an emergency. Unfortunately, delegation is a process and one that cannot be shortcut. To the first point above, support gaps must first be identified before they can be filled. Addressing said gaps may feel a little like how “one eats an elephant, one bite at a time”. Understand that prioritization will be critical here, and some things “may need to remain broken” for a time. A good consultant can help your organization determine that prioritization, but regardless, the gaps will unlikely be able to all be addressed at once and there will be a transition as the organization works towards future state.

Additionally, pioneers and/or the senior leaders who support them, must learn to manage systems or put another way, how to get work done through other people. This is a set of skills not just a specific action including how to design processes and iterate on them, collaboration with others, giving, receiving, and implementing feedback, and the all-important documentation, documentation, documentation.

At the end of the day, Superman was fiction—a myth that one person could handle infinite responsibility without consequence. However, the most successful pioneers recognize that real power comes from building systems that outlast individual limitations. When leaders learn to create robust structures, delegate effectively, and develop others to carry the mission forward, they achieve something far more powerful than any fictional superhero: a legacy that multiplies their impact and outlasts their tenure.

¹Zain Jaffer, ” 1 in 2 Founders Reported Experiencing Burnout in 2024 — Here’s How to Prevent It From Happening to You,” Entrepreneur, March 20, 2025, https://www.entrepreneur.com/living/scaling-a-startup-avoid-the-burnout-trap-with-these/487247.

²Jackie Vanderbrug, Jill Kickul, and Mark Albion, “What Makes Entrepreneurs Burn Out,” Harvard Business Review, April 4, 2018, https://hbr.org/2018/04/what-makes-entrepreneurs-burn-out.