Navigating the 5 Phases of Executive Transition

CEOs and CHRs have a critical role to play in executive onboarding – making it okay to ask for help.

I have seen many very highly accomplished and successful executives go into a new job full of the possibilities in front of them, only to hit a wall that they were not even aware was there.

Unfortunately, today we live in a culture where CEOs, COOs, and other high-level executives are supposed to know all the answers. They are not supposed to ask for help from colleagues, employees, and coaches. They often look at asking for help as taking one step down in status or making themselves vulnerable in the eyes of others.

Yet we know that the best Silicon Valley CEOs all have CEO Whisperers who they have reached out to for help—Larry Page, Jeff Bezos, Steve Jobs, and many others.

I have written that the CEO and HR have a critical role to play in executive onboarding. It is they who can make it okay for the executive to seek help. 

A coach or mentor, either internal or external to the company, can make all of the difference in navigating the chessboard of the first 100 days.

In coaching many executives during this critical period, I have discovered that there are 5 phases to the executive transition, each with its own problems and opportunities and working with a coach or mentor, can make all of the difference.

1. THE COUNTDOWN PERIOD — failing to prepare for the job before you start

This is the time to prepare for the journey before you start the job (usually at least a month). It’s important to spend time on preparation, because once you get to day one, you will be rushing from meeting to meeting, drinking from a fire hose, and will not have the time. Before you get started, it is a good time to think about what your strengths have been as a leader in your previous jobs and how these might be vulnerabilities in the new one.

For example, a top-down leadership style may have worked in your old job where you were the top dog and the ultimate decision-maker, yet a collaborative style is what will be required in your new job where you may not have direct authority.

It’s also a good time to create a learning agenda for your new posting that will help get you ready for day one: 1) What do I know about this company and what do I need to learn? 2) What do I know about my boss and job, and what do I need to learn? 3) Is there anyone I can talk to who can mentor me on these things?

I usually advise clients to create a first draft of the First 100 Day Action Plan in the countdown period, so that they can hit the ground running, even if they don’t have all the information at this time.

2. THE HONEYMOON PERIOD — the problem of overconfidence

This is the first one to three months “fantasy” period where everything appears to be going smoothly. This can lead to overconfidence, causing executives to over-reach their job mandate, or to make mistakes in negotiating the political chessboard and culture.

This overconfidence results in people failing to ask for coaching or getting 360 feedback, which often leads to them bumping into obstacles they didn’t know were there.

A CEO hired a CFO to help the COO get some major deals over the line. The CFO caught heat from the boss when the first missive he sent to the organization was to severely cut down on Christmas party expenses.

Another example is a newly hired SVP of Strategy in a software business who came up with a game-changing product development idea and went to the executive committee without realizing he was starting a civil war with the SVP of Engineering, who thought product development decisions were his sacred control ground.

The great anthropologist, Margaret Mead, once said, “In the end, culture is all determinant. Violate at your peril.”

A CEO of a “spirits” company took his top team, including the EVP of Global Sales, on a trip to Russia to profit from their “liquid gold.” The EVP thought the trip went well, but when he got back, he discovered that his boss was pissed off, “You have already earned yourself a reputation as a party animal, staying up to 2 am drinking.” It turns out that in his previous company, the philosophy was “work hard, play hard.” In the new company, people went to their rooms at 8 o’clock and were ready to go for a five-mile run before work in the morning.

I strongly advise making sure that friendly, informal, frequent feedback is just around the corner. “How am I doing?” Make sure to ask for near brutal candor. If someone says you are doing great when you really not, it fuels overconfidence and you don’t learn anything.

3. REALITY BITES — the problem of disillusionment

The first signs of disillusionment come when you realize that your new boss is really a combination of Dr. Jekyll and Mr. Hyde. It’s impossible to please such a boss, not only because of their bipolar personality but because they change the rules every day. For example, a client Ram Serif was hired by the CEO as CCO (Chief Commercial Officer) of a government-owned company in India, much like Verizon or AT&T (home phone, TV, internet, and wireless).

The CEO ran the company like an absolute monarchy and one day put his arm around Ram in a very paternalistic way, “I want you to know that I am not only inspired by having you on the team, but I am also fully empowering you to do everything humanly possible to increase profitable revenue.”

However, the CEO didn’t tell Ram that all he really cared about was new revenue from new clients to increase market share. When Ram decide to increase prices by 20% to drive EBIT, he found himself being called to the boss’s office for a tongue lashing.

Coaching someone in this kind of situation usually involves preparing them for having a candid conversation with their boss or others. You must stand up to the boss and be respectful at the same time. If you don’t, you will spend the rest of your life in the company disempowered and demoralized.

4. ADJUSTMENT — the problem of adaptability

As a coach, I tell people that when reality bites, they have two choices. One is to give up and start looking for a new job (not a pleasant thought). The other is to find a way to adjust to the new situation.

For example, as a new executive, you may have a boss from hell, but you will get along better if you get coaching on how to work with that person, thinking in terms of how to make the boss successful, and not letting that person’s idiosyncrasies bother you.

The same applies to your new team. Instead of decrying the fact that you don’t have a team of  ‘A’ players, you can adjust your attitude by telling yourself you’ve got to play the hand that you’ve been given and bring out the best in people.

If you are willing to make these kinds of adjustments, relationships will start to gain traction, results will start to come in, and confidence will be recovered. If you are not willing to make adjustments, you will be fired and told something like, “Don’t let the screen door hit you on the way out.”

5. INTEGRATION — you’ve made it!

This occurs when executives successfully run the gauntlet for about 12 to 18 months and then wake up one day to realize they are in the right place. The signs leading up to this revelation are having created a good relationship with the boss, hitting sales forecast and budget, and having a good idea of how to navigate the political chessboard and culture.