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The Ins and Outs of Executive Coaching & How They Can Make You More Successful

As an entrepreneur with 6 businesses under my belt, I have learned that having a business takes open and honest conversations because the top can be a lonely place. As an executive leader, you might sometimes feel like you can’t or shouldn’t have conversations with anyone in the company because they can easily take your conversation the wrong way. Depending on the conversation, you may leave them wondering if the company is in financial trouble, or they take your frustrations on and suddenly begin to look and act differently towards you. It is a common practice for a business owner or executive to connect with someone in the company and turn them into their personal confidant, sounding board or advisor, especially when they are looking for some type of advice.

Firstly, one problem with that is that maybe you were venting about someone or something that happened. Perhaps you were brainstorming about some ideas, your concern about sales and revenues or maybe you were sharing about your personal life. Whatever the conversation, it can create several issues. First and probably the most important one is that you are now burdening someone within the company with your frustrations, struggles, thoughts and concerns. In most cases, that person is not equipped to handle those conversations. They naturally want to help, and they try to give advice, but the advice has no depth of experience. Because they have no one else, the business owner or executive continues to rely on this person more and more, which can create an unhealthy relationship.

Secondly, you are now creating distractions and anxiety for that person. They feel special that you have confided in them and may even begin to act differently around others, almost with a sense of empowerment. They know something no one else in the company does, and they like how that makes them feel. The more they think about it, the less productive they are, and the more distracted they become, until one day, as the owner or executive, you have to have a difficult conversation with them about their work and/or their lack of work. Suddenly, you’ve created a situation with a key person that never should have happened. They feel betrayed, let down and demoralized. So, although, as the owner or executive, you may feel better, you have now created tension with one of your people.

This is a sad but common story, and I would bet that a lot of business owners/executives have similar stories. In reality, what I just described is only one scenario. Business owners and executives have to not only have someone that they can talk with, share ideas, and vent frustrations, but they need someone that can make them better. We all have weaknesses, and you either need to learn to get better with those weaknesses, or you need to surround yourself with someone that fills that void for you. But first, you must identify those weaknesses. You can find the solution to your unique situation with an executive coach.

To break down how they are equipped to help you solve business problems, let’s talk about what they do.

What is an Executive Coach?

An executive coach provides a confidential and supportive sounding board for their clients. They ask questions, challenge assumptions, help achieve clarity, provide resources, and sometimes, with permission, provide advice. The ultimate goal is to help the client find an acceptable answer for the situation. They often guide and help interpret situations and behavioral assessments and conduct confidential interviews with employees to help understand the executive, leadership, business and concerns. Thus, giving the coach a more well-rounded understanding which helps to provide more meaningful coaching.

Who Hires Executive Coaches?

In the past, a company would hire executive coaches to come in and fix broken executives. Today, most companies hire executive coaches to invest in their top executives and high potentials. It’s no longer a disgrace to have a coach; it’s a status symbol. The coaching foundation recently published that statistic that shows 55% of all privately held companies hire an executive coach, while 34% of public companies do the same.

While executives can hire their own coaches (usually CEOs or business owners), it’s more common for companies (often the human resources department) to recommend a coach to an executive as a part of an executive development program. The employee could be newly promoted (transition/executive coaching), learning to deal with several challenges (usually involving employee relationships), or developing them for more significant roles. Coaches are sometimes hired to correct behavioral problems and help leaders resolve interpersonal issues, making them better leaders and executives.

The Framework of the Coaching Process

While there are many variations, executive coaching usually involves a series of levels; others may call them phases. It starts with onboarding and then rolls into 4 different levels. The first level is the Tandem level, where we understand the person, the company and the issues, helping them identify the areas that need work and begin the change process. From there, they move to the Accelerate lever, which includes spending time on personal assessment, understanding their weaknesses, and then helping them learn and grow in those areas. The third level is Momentum, where we set personal and business goals, then track the progress, identify issues or stumbling blocks along the way, and learn to make adjustments to achieve those goals. The fourth and last level is the Pilot level. At this point, they should feel like they are in control. The executive coach provides periodic check-ins or as-needed support with the executive’s manager. The process is potentially over when the development goals are achieved, or the coach or pupil decides it should stop. In our experience, the ongoing relationship can last for years. It is a journey, and everyone is different, so when people ask how long the coaching lasts, I usually say it is up to the individual and the degree of change required.

A couple of final notes:


All conversations between the coach and the client are completely confidential. If an organization pays for the coaching services, we can provide periodic status updates (dates, levels, milestones achieved, etc.), but no personal or in-depth information is shared without the executive’s permission.

How meetings happen

Face-to-face is always preferred but not always possible because of the geographical separation. When this occurs, video calls occur, with two (2) on-site visits per year. These are usually 1 - 2 day out-of-office visits to review the past six(6) months and plan the next six (6) months.

Pull the Chute is the premier business, executive and leadership coaching firm. We help business owners and executives be the best they can be; in turn, this helps them to grow their companies to new and exciting heights. If you are thinking about hiring an executive coach, let’s get on a call and see if it makes sense for you. Use my calendly link to set up a free consultation:

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