Leadership Transition

Have you thought about choosing
successor for your business?  


Or are you building a team of
executives to take it to the next level?


Either way here are 8 key questions
you must first answer to be successful.


This is a lazy job description for a new leader. It means you have not thought this new position through. So you want to hire someone who will do things your way, with the same organization and people, who has your management style, and will get a better result. This is the definition of insanity. No one is a better you.
A job description for the new leader is important – and easy. The important job description is yours. What will be your new function, your new responsibilities, and your new duties? If you don’t have a detailed job description you will end up falling back into your old position and vying with your new leader in his/her job.

A goal is something to be accomplished.  An outcome is the result of a successful goal.  It provides context to the goals.

Your new leader should be selected to complement, not duplicate, your experiences and skills.  In order to maximize success, both of you need to define and agree upon a successful outcome, not simply goals. 

The metrics and targets your new leader will track must be mutually agreeable to both of you. There will be disagreements and the “soft” things that take time (e.g. branding, customer engagement).  But if the two of you fail to come to fierce agreement on the “hard” metrics – and how to interpret them, you will also be in fierce disagreement on how things are going.
At least part of the motivation for a change in leadership is to get things done that have never gotten done before.  But before you simply assign these things to the new leader, first take the time to honestly assess why you haven’t done them.  
Was it a lack of time or resource?  Missing expertise or experience? Or something else?   Was it you?
Have you considered that you were the reason. Perhaps because of a reluctance to deal with a long-time staff member, or unwillingness to make a change in process. Maybe you didn’t want to be the “bad guy.”. If nothing changes, your new leader won’t be able to do them either.  
If you want those changes –give your new leader the ability to make them.  Or you may have to let those things go.
One thing is sure when a new leader comes in –things will be different.  And you must be able to clearly differentiate between different and failure. In order to be able to do this, failure must be defined.  
You and your new leader need to be in agreement not only on what success looks like, but also what is failure.
Transitioning to a new leader is a serious commitment, on the part of the existing leader, the staff, and the customers.  A hallmark of commitment is for both parties to know there is no “plan B,” no soft landing elsewhere in the company.  This is key to give the new leader a fair opportunity to succeed.
You and the new leader jointly share responsibility for the result.  The new leader should not expect to be rewarded in the event of failure, and neither should you.
Being a leader and running an organization is a big responsibility.  Taking over leadership for an organization is no less a challenge and bears a considerable risk of failure. Reward for the new leader defined up front along with success  Simply being allowed to keep one’s job is not a reward.
Now that you’ve seen the questions, consider something else.
It takes the average business leader 3 attempts to successfully identify and install their eventual successor. Imagine the impact of this on your employees, your customers, and not to mention on the failed candidates!

“Hope is generally a wrong guide,
though it is good company along the way.”

George Savile

I’ve worked for eight different entrepreneurs, been an executive for six of them, and ran companies for four. I’ve been both the successful and the failed candidate. I know what this is like… for both parties.


As a Houston Business Mentor and Executive Coach, I can help.

Contact me to see how.


“The stories, imbedded in “ELEPHANT TALES “, depict in a humorous way realistic encounters between CEOs and their Organizations. “ELEPHANT TALES” is a required read for any CEO interested in improving his/her leadership by understanding the relationship between the Elephants, the Ants, and the Mahouts. There is much wisdom between the lines of each story. CEOs skilled in understanding what these stories reflect are better prepared and more able to discern and focus on the appropriate courses of their Corporate Decision Making.”
A. "Butch" Madrazo
President and CEO / MMM Enterprises, Inc.
"(Elephant Tales is a) wonderful book. Very thought provoking. I can definitely see the value of presenting one of these stories to a leadership team for discussion and potential issue solving as the opportunity presents itself. As a professional who also works with Entrepreneurs and is one, these stories are on point and typical of what I see on a regular basis. Sometimes being too close to the problem is the problem. Stand back and look at it from an outsider perspective. Does it look the same? How many story related events have you experienced or caused? I definitely narrowed in on a few that I could relate to. Funny how much alike most business's are. It's those leaders that recognize it and do things differently who win."
Salty Thomason
President / LeaderShift, LLC
"I've known Keith for years, and his ability to translate deep leadership lessons into easily-relatable messages has been part of his "special sauce" as long as I've known him. I'm so pleased he collected his messages into "Elephant Tales" -- it's an inspirational read, filled with practical, powerful leadership advice. My advice? Get a copy for yourself, and one for all the members of your team. Thanks, Keith!"
Bob Tipton
Chief Executive Officer / R S Tipton, Inc.
"I've had the pleasure of working with Keith for the past few months and it's been an incredibly valuable experience. Keith offers a lot of creativity and wisdom when tackling business issues. Keith inspires new ways of thinking and is easy to collaborate with which inspires the best possible outcome to complex business matters. I consider Keith's ideas and feedback instrumental in many of the positive changes we've made this year."
David Balzen
Chief Executive Officer / SalesStaff, LLC
"I’ve had the pleasure of working alongside Keith over the last five years as an IT service partner and most recently as a client of Closing Strong. Keith’s intimate knowledge and understanding of the challenges of the legal technology and consulting industry has been invaluable and would be difficult to replicate. His perceptiveness and insight based on years of direct leadership experience has provided me with the guidance needed to make changes that positively impact the bottom line. One of the most important things my sessions with Keith provide, is the dedicated time to review my challenges and assess my decisions. Keith is quickly able to understand the situation, drill down on the actual issue and make me confront them. In the very short time we have worked together in this capacity, Keith has helped me to identify and focus on some of my biggest challenges towards developing a strategy for growing the firm without compromising our values. I have no hesitation in recommending Keith. I am confident I’ll continue to leverage his guidance as we advance to the next phase."
Angelo Whitfield
President - Sophus Consulting - Public Sector Information Technology and Services Consultant / Sophus Consulting
"Keith is a true motivator and leader. Keith obtains a great ability to break a complex business into simple, easy to understand, business strategy.”
Matthew Blake, MBA
CEO / Franklin Data
"For the past few months I have been meeting with Keith and find our conversations to be the highlight of each month. I leave each meeting feeling like I have a heightened level of clarity, inspiration to continue challenging myself as a leader and motivation to think about things in a new way. Keith provides such a balance in his coaching: he gives advice, shares anecdotes from his extensive personal experience, asks the right questions, pushes me to think and act boldly and provides genuine encouragement.”
Amanda George
Consultant / Sterling Associates
"Keith is a true leader; he’s got great, natural leadership skills. My experience as an officer in the military has confirmed that leadership can be taught – to a point, beyond which instinctive leadership traits emerge, but only from the exceptional leaders. That’s where Keith shines. Keith creates an inspiring vision for organizational goals. And then he knows how to inspire and motivate his team to achieve those goals. He takes teamwork to a whole new level. Keith’s team members routinely exceed their performance expectations.”
Chip Cooper
E-Commerce Attorney ✔SaaS Attorney ✔Custom FTC Compliance Programs ✔ Author ✔ Speaker
“Keith has proven over time to have the perspective, vision and patience in working with others to build teams and accomplish goals for the business he runs. He leads with passion, focus and determination.”
Ernie Rapp
President & PCCA Vice President of Business Development / PersonalMed
“I’ve known Keith since 2001. I have had the pleasure of working with him in a variety of settings, including as members of an executive round table where we collaborated on the challenges of building our respective businesses. First, he gets it: growing a business, leading an organization, managing diverse organization, managing diverse individuals, inspiring results, setting uncompromising high standards and ethics. Then, repeatedly, he delivers the results. Keith is someone I trust and rely on for counsel and feedback, and our relationship is one that I highly value.”
Stephen Sweeny
Chief Operating Officer / 3Coast
"Keith Okano brings a clarity-of-thought to the executive team. He has a measured and seasoned approach to problem solving, a highly responsive, yet fair and even-handed style when dealing with crisis, and an overall intuitive sense of what it means to be a leader."
Mike Dalton
SVP Worldwide SaaS Software Engineering / BAE Systems
“Keith Okano has this unique and uncanny ability to make everyone feel comfortable, important, and as though their opinion is truly valued. He communicates as openly and effectively with a client or partner as he can with one of his own staff. He can easily discuss details at a technical level, business level, market level, or executive level. He is thoughtful, creative, thorough, and a visionary.”
Wayne Ford
SVP WW Commercial Sales / Kofax
"Keith has the ability to learn new businesses and organizations quickly, and to adopt their missions as his own. However his true gifts lie in being able to become part of the team in developing the appropriate strategy and goals, and define the processes and KPIs needed to fulfill it with great efficiency."
Al Mueller
President/Owner / Excellence in Giving
"Keith truly values individuals, with all their strengths and shortcomings, and enjoys lending his experience and long track record of success in support of others."
Mark Poag
Managing Director / FitzRandolph Gateway Ventures
“Keith's decision-making ability, confidence and continued support are key in helping get through difficult situations while continuing to contribute to the bottom line. His professional and very approachable leadership style streamlined many operations and promoted continued unity and morale within the organization.“
Lentz Ferrell
Director ISS (ret.), / Silverton Healthcare
“Keith has the ability to get an entire company focused in a positive direction while empowering managers to take responsibility of working as a single team. Keith is fair with outstanding business ethics.”
Brad Thompson,
President, Epex LLC