11 Rookie Mistakes Business Leaders Wish They Never Made

As Winston Churchill said, “All men make mistakes, but only wise men learn from their mistakes.”

Being a leader comes with a lot of responsibilities and pressures. Not only are you accountable for your business’s success, but you also have to maintain a positive work environment, foster collaboration among teams and other leaders, motivate employees and troubleshoot problems. Mistakes can be common, especially in those early days of leadership.

Luckily, here at TAB we run the world’s largest network of CEOs who are willing to share their early business mistakes so you do not have to repeat them. Read below for 11 rookie mistakes our business leaders want to help you avoid.

1. Keeping All the Monkeys on Your Back

Early on in my role as a leader I had the tendency to offer a solution to every issue that came through my door. I thought it was my role and it was certainly efficient. I was able to handle multiple crises every day and nobody had to linger in my office. I soon learned that I became the bottleneck on issues that were surfacing, and I owned the results of resolving every issue. The business was running me vs. me running the business. The office mantra became “let’s go see what Byron wants us to do.” The solution and results became my problem not theirs; they were simply following instructions. 

I do not remember where I heard it, but I never forgot the principle of the “transfer of monkeys.” The basic principle is that when an employee brings a problem or an issue to you, they are wanting to get the monkey off their back and throw it onto yours. Your goal as a leader is to keep the monkey on their back and keep it off of yours. They need to maintain ownership of the solution. To help train my mindset, I put a picture of a small monkey on the corner of my monitor. When someone walked into my office, I would see the picture and mentally visualize a monkey sitting on their shoulder. My goal was to keep the monkey there. It mentally changed my approach from offering solutions to asking questions. 

It took time to cement the concept in my mind and in the minds of my staff, but it revolutionized my management approach. 25 years have passed since I first heard the concept. The image of a monkey is still as real today as it was the first time I heard it. Are you finding that your day is filled with fighting fires and you are the one providing all the answers? Is your staff not taking ownership of solving problems? Think about the monkey. Evaluate if you are willingly taking on the monkeys from everyone in your business.

Byron Roth, Owner at The Alternative Board, Bethlehem, Pennsylvania

2. Tackling International Markets Too Soon

A common mistake seen in the beginning of many technology companies is trying to address international markets before having consolidated and succeeded in their domestic market.  International markets are more complex than the domestic one, and to face them the company must have tuned processes with successful references.

Antonio Rodríguez Chaparro, CEO at The Alternative Board España centro/sur

3. Trying to Win the Popularity Contest

I became a CEO at 30-years-old. I have learned so much in 3 ½ years and have made more “rookie” mistakes than I can count. When I moved into my role, I had a vision that I would be an approachable and likeable CEO. Well, what’s true is that my approval seeking needs came crashing down quickly. I learned that I would need to make hard decisions that would have varying impacts on my team and would not please everyone. Sometimes I found that my decisions wouldn’t please … anyone. When possible, soliciting feedback, providing context and communication helps BUT may not be enough. I have developed a new handrail to help keep me grounded while trying to look at situations objectively. With my background in organizational psychology I ask, “If I were a consultant to this company, in this situation, and I was looking in, what would I recommend and why?”

Dani Kimlinger, CEO at MINES and Associates and TAB Member

4. Not Being Comfortable With Silence

Your entire climb to the top, whether it is in a classroom or business, is often based on the ability to answer questions correctly. When I first became a C-level executive, in meetings when a particular challenge or opportunity was presented to the group, I would always be the first to chime in. It overflowed into my leading of teams, where I would pose a question to a group, not get a quick enough reply or immediate answer, so I would fill in the silence with “my brilliance.”

Today, I am much more comfortable with not being the first to speak (in fact I rarely do), or ask more questions around a topic to help others shine. If you are always the first to speak or monopolize meetings or conversations, try reversing it and speak less and listen more, you’ll be surprised by what you hear! Unlike school, the brightest person in the room is often not the one with the clever answer, but the clever question.

Jodie Shaw, CMO at The Alternative Board

5. Confusing Being Active With Being Productive

Time is a finite thing, so everything you choose to do comes at the expense of being able to do something else. Sometimes, we confuse business activity with being productive, but some of those things keeping us busy are blocking more important things to do. A cure is to start with the end game in mind and ask yourself with each choice of tasks, “Which one will really advance me towards my goal?” It's a universal challenge, so don't judge yourself too harshly, but be comforted to know that each better choice moves you forward faster.

Wm. David Levesque, President at The Alternative Board - Rochester

6. Not Motivating Employees

I have seen this more than once. Owners want to make sure their employees are “working,” so they limit their compensation to hourly, and insist on tracking the hours they work. You’ve no doubt heard “What gets measured, gets improved.” When owners do this, they find people putting in their time without regard to their performance, contributions to the department, or company objectives. These owners eventually realize offering a reward for performance can help engage employees in quality work that advances business goals. This could be sales, production, quality (waste) or any number of metrics. Often, they find their TAB Boards can help them define and implement effective measurement and reward systems.

Bob Dodge, Partner at The Alternative Board - Denver West

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7. Waiting for Permission

In my first leadership role in the telecom software industry, I had lots of good ideas and was very intent on proving I could do the job and do it well. I would think through solutions and send an email to my boss to get his ideas and approval. After a few months, he pulled me aside and told me he was going to assess my performance based on the number of emails he got from me. If he continued to get the same number of emails I was currently sending, my performance would be rated poorly, but if they were dramatically reduced, my performance would be rated very high. He explained that I had solid ideas and a logical approach to problem solving and that I didn’t need his permission. I should simply go ahead with my plans. This was a valuable lesson for me and gave me the confidence I needed to succeed.

Laura Drury, CEO/Owner at TAB Denver DTC and Colorado Springs

8. Being an Obstacle in the Process

The enthusiasm for being a client advocate was a strong one for me. The role of project manager, for me, meant doing the right things and getting them done on time every day.  However, it led to this feeling that I needed to be in control to make sure all of these expectations were met. The unintended consequence was that my hands were all over the work for every client. The result was that my misinterpretation of control became the chains that bound me and the company from growth. I learned that the real control was in being the teacher, and helping others to understand the expectations of accountability in the process. The best takeaway for me was that this effort of letting go wasn't about giving away leadership.  It was about accepting the job of creating paths instead of being the obstacle for others in the process.

Bob Green, Owner at The Alternative Board, North Shore

9. Failing to Impress

Talk about a rookie mistake.  Here's a doozy. It was the 2nd job of my career, a Director position at a major entertainment company based in New York City. It was my 2nd week on the job and I was asked by my boss, the VP of Marketing,  to join her in a meeting with her boss, the SVP of Marketing, a well-known, mythical person in the industry. The fact that I was asked was a big deal.   

The meeting was in a conference room that included one of those large conference room tables that sat 15 or so. I took my seat in the back of the room, not even at the table, so other, more senior people could have better seats. The SVP walked in and before the meeting started, there were two new people in the department so we did introductions. My boss introduced me first and before I got a chance to say anything, the SVP said to me, in front of the 20 other people in the room, "John, you should never chew gum in a business meeting so please take that out now.” I was humiliated. I immediately took the gum out, apologized, briefly introduced myself and did not move or say a word for the next :55 of the meeting. I totally forgot that I was chewing gum but what a lesson. From that point on, I've never chewed gum again in any business setting. 

But the best lesson I learned was: after the meeting, I went to the SVP's office (with my tail between my legs) and apologized to him in person.  He was very appreciative but I later found out from my boss that he told her that it took a lot of guts for me to apologize personally to him and he had a lot of respect for me for doing it.  I stayed at that company for 7 years and the SVP and I had a great relationship.  The chewing gum incident taught me that how you react to a negative situation, regardless of your experience/seniority level, can have a huge impact on your career. I made something good out of a bad situation, and having the courage to humble myself the way I did was one of the most important lessons I learned in my early career.  

John Mousseau, Owner at The Alternative Board, Jersey Shore North

10. Wanting to Be Everyone’s Friend

It was my first time working with a particular VP of a large company. In any new business relationship I would always default to “I want us to be friends.” After about 20 minutes in a meeting where I was called in to help solve some big issues he looked at me and said, “Steve, I really don’t need any more friends. What I really need from you is help taking care of this problem.” At first, I was a bit shocked. I then realized I was not doing a good job reading his behavioral preferences, but had defaulted to thinking everyone had the same preferences as did I. Now I look for signs and cues that help me understand the preferences of the other person.

Steve Drury, President/Owner at TAB Denver DTC and Colorado Springs

11. Focusing on Perfection

When I was a new manager, I wanted everything my team did to be perfect. When we had to respond to an RFP or create documentation, I pushed my team to work late to get every word right and every “t” crossed. Since I was young and did not have a family at home, I did not take into account that my team members had responsibilities outside of their job. One of my employees pointed out that nothing is ever perfect and that the time spent getting too perfect is not worth the cost of work life balance. I took this to heart and found that the work products did, in fact, meet customer needs without perfection and that my team was happier in their jobs.  This lesson has stayed with me throughout my career and has resulted in happier high performing teams. Striving for perfection does not equal perfect!       

Lisa Marie Maxson, CEO at 10X People and TAB Member