You Won't Be Promoted Until You’ve Prepared Your Successor

preparingyoursuccessorTime and time again, talented, capable executives get passed up for promotions because there isn’t anyone to take their place. When speaking to their bosses I often hear things like, “I need her there... Who else can do what she does?” and “If he got promoted, it would leave a huge vacuum.”

We are coming to the end of a new year, a time when many of us are thinking about what goals we want to achieve in the new year.  One of the top goals I hear being expressed is to be promoted.

If that is your goal, then please consider which of your team members you will train to succeed you.  Also consider how you will train them.

Here are some suggestions:

1. Speak to your boss and key stakeholders about what they would like to see in the person who takes your role.

Your successor will need support from key stakeholders, including your boss, if the transition is going to be a success.  A conversation with them ahead of time will allow you to gain buy-in from them as they see the traits develop in the person you will be choosing.

2. Create a job description based on the reality of your role.

How much of the original job description is what you do day in and day out?  Writing a realistic job description will help your successor tremendously.

Be sure to focus on what is the most essential part of the role and what are the soft and hard skills necessary to succeed in the role.  Also emphasize the appropriate points which key stakeholders said they wanted.

A question I sometimes use with the executives I coach is, “If you could hire a more idealized version of yourself to take over your role, what characteristics would they have?” (BTW- your answers to that question are great for determining what goals to reach for while you yourself are in the role.)

3. Determine who will be your successor and get their buy-in.

After you have the job description, look at your team.  Who is likely to be able to match that description and exceed it?  It may not be the direct report who is excelling the most.  Be sure to think through who has the best potential to far exceed the job description.

Then go and see if that person is interested in being trained to take your role.

If you have a huge role that needs to be broken up (and your management supports that decision), then focus on a couple of successors.

If the best person to take over is not a part of the current team, be sure to keep your direct reports informed.  As you bring the new person in, help your direct reports understand your rationale, and explain how they can help the new leader succeed.

4. Train incrementally.

Give your potential successor opportunities to really stretch their skills.  Have them assume much more of a leadership role than they have had in specific projects.  Coach when necessary.  Then have times to debrief afterwards.

5. Create milestones.

Your successor will probably want to know when they will be viewed as being ready to assume the leadership role.  The more tangible you can make these milestones, the better.  This will help stakeholders to buy in even more.

6. Focus on the future.

Assume that the current problems your team is facing will be resolved, and that there will be new ones in the future.  What principles of problem solving does the team need to learn in order to make more effective decisions?

Moreover, think about where the overall organization is heading.  What are some key things your successor needs to know and do in order to align with the greater company’s focus?

7. Consider that your successor may not be a clone of you.

There are times when replicating yourself is advantageous, and there are times when having someone different from you take over is exactly what a team needs to move to higher levels of cohesion and performance.  What do the team and the overall organization need for this next step?

8. Communicate to your team early that a change is coming.

Knowledge of an imminent change can often lead people to fear the unknown.  You can minimize this fear by informing your team as soon as it is appropriate, to help them adjust.  Also, be clear about expectations, so that everyone knows what to count on.

9. Use job shadowing.

Your successor needs to know that they are being watched by those above the team members.  They need to learn to be the leader before they get the position.

Job shadowing will help them see a template in you.  If they are a different personality type than you are, and/or have different gifts than you do, then use some of the shadowing time to discuss how they would have handled things in their style.

10. Set your successor up for success.

Determine what win your successor could have before assuming their role that would help the team to fully embrace their leadership?

However you can set them up for success ahead of time will pay dividends in a smooth transition.

11. Offer to be a mentor/coach for awhile after they’ve assumed your role.

Some successors may not come to you as much as to others.  However, it will be great for them to know that you are there until they get their legs under them.

Succession is key to getting promoted.  When you have a replacement, your boss and others above you will look for opportunities for you.

If there isn’t someone to take your place, don’t be surprised if getting your next promotion is more difficult than you thought.

Chew On This:

  • If you could have a more idealized version of yourself take over your role, what characteristics would they have?


Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

*This blog is an amalgamation of a few different clients.  No one single client is being singled out.

How to Recover from Major Setbacks, Part 1

how-to-recover-from-major-setbacks-part-1Back in 2008, I had a client who was a star performer at his large company. (As with all my posts, I have his permission to use his story.) When you hear his story, you think his parents should have named him Midas, because everything he touched turned to gold.

He went to all the right schools and earned full scholarships.  He landed in all the right jobs and climbed quickly.

He had huge accomplishments for someone his age.

He was not only very smart, but he really knew how to relate well to others.

It seemed like he had the complete package.

When I asked him about his failures or his setbacks, he thought for awhile and then mentioned things that seemed so harmless and inconsequential that I wanted to say, “That’s it?”  I thought to myself, “Wow, I did not know people like you existed.”

If you noticed in the opening line what year this was, you could probably guess that in 2008 he got a taste of serious failure.  When the recession hit, his company was devastated.  They laid off many, many people.

He was assured that he was not going to be cut.  But as the recession lengthened, that is exactly what happened. He was released from employment.

After coming out of his boss’ office the day he got that news, he was stunned.  But he was absolutely shocked at those who got to keep their jobs. He could not understand why he was let go and they were not.

For the first time in his life, he did not make the cut.

When he came to my office he was noticeably numb.  It seemed he was trying to harden his heart so he would not feel the pain that he was in.

It was obvious that he needed to process what he was feeling, but he was unwilling.

His numbness went to rage, then to depression, then back to numbness, and then his emotions just bounced around.

As much as I tried to encourage him to describe what he felt, all that came out of his mouth were facts.

I stopped trying to encourage him to describe his feelings, and focused on empathy instead.

He talked for another 10mins and then said he needed to go.

He never returned.

That was the start of a long, bitter, downward spiral for him.  Even though he landed on his feet before the severance package ran out, I learned a few years later that he had never fully recovered from that setback. He remained angry and bitter.

Recently, he gave me a call and wanted to start up again.

Now he is actively fighting to heal and continue his growth.

He sees how much was stolen in the last eight years and doesn’t want to lose any more.

It is true the vast majority of us don’t have a story like this.  However, we have been impacted by career setbacks.  There may be one setback in particular that stands out.

Have you fully recovered from it? 

If you don't know, then ask yourself:

  • What were you like before the setback happened?
  • What has changed for the worse?
  • Are you still playing it inappropriately cautious?
  • How has your life been impacted?

If you are not stronger and better, then you probably have not fully recovered from the setback.

Here are 5 steps that may help:

  • Describe the Pain You Feel Without Using Facts

Recognize the shock, denial, hurt, betrayal, grief, depression, anxiety, and whatever other emotions you feel from the setback, and fully embrace them.  You were meant to feel what you feel.

In order to process your emotions, stop Judging yourself, Accusing yourself, or Calling out facts (J.A.C.- yes, you can laugh now), and just M.O.P. -- that is, describe your emotions using Metaphors, Other emotions, and Physical sensations.

The more you describe what you feel (not think), the more you will sense yourself going through the emotions and emerging stronger on the other side.

I like to MOP via journaling so I can catch when I start to JAC.  Others like to MOP with others. So for example, during one coaching meeting an executive’s MOP was:

“I feel angry like a bull seeing red in an arena.  I feel frustrated, annoyed, enraged, anxious, really hurt and completely betrayed.  I feel like a dad who lovingly cared for and raised his son, only to have the son spit in his face and run away when he most needed him. My heart is pumping fast.  My breathing is heavy.  My blood feels warm.  I can hear my heart pounding in my ear.  I am fighting back tears.”

His MOP continued from there for a bit, and then he got calm and wanted to make a plan to move forward.

When you describe your emotions this way, don’t be surprised if they intensify before you get to a calm place.

By the way, can you guess what happened that led that executive to feel all of that?

I will share why he felt all of this at the bottom of this post.  Don’t peak!

  • Stop the Self-Flagellation

I can beat the crap out of myself when I have a setback.  Man, I am hard on myself.  But I have learned from personal experience that beating myself up only brings me more problems.  Instead, I need to do step one above, and then move directly to step 3.

If you don't want to bypass the self-flagellation, or are not ready to let go of it, save the rest of this blog for when you are.

I've found that when I'm in a place where I don't want to grow or heal, it does no good for someone to give me helpful tips or advice because I will never believe it will work. My desire to shame myself is too strong.

If you find yourself there, then MOP what it's like to not want to grow or heal, until you find yourself wanting to heal and grow.

If you need to own your setback to your boss, then read a previous blog post for tips on how to handle that conversation.

I’ve seen the power of complete ownership, with no marketing, at work in my life and in the lives of others.  Whoever you need to own things to, do it.

One of the side benefits of such ownership is that you will start to gain control over the setback instead of letting it control you.

  • Flip Tool- How Could It Have Been Worse?

Now take the setback and really exaggerate it out.  How could the setback have been worse?  Really get into this.  Give it details.  Don’t be ridiculous with the step, but really look for ways that it actually could have been worse.

Don’t just describe the facts of how it could have been worse, but describe what you would feel if those facts had happened.

Once you have it clear in your head how it could have been worse, and you have described your emotions so well that you are actually feeling them in the present, then go to step 5.

  • What Good Might Have Come If The Absolute Worst Had Happened

Now with the more horrible version of the setback in mind, create an exhaustive list of what possible good could have come if the absolute worst had happened.

At first you may not be able to come up with much, but stick to this step and don’t bypass it.

You want to stretch yourself here.

Some questions that might help you get unstuck, and put more potential good on your list, include:

  • How could people be supportive?
  • What opportunities could arise through it?
  • How would I be better, having fully dealt with everything I experienced?
  • What could I learn through going through this process?
  • How would I be better if I learned it?
  • How would my character grow?
  • How would I be able to help others because of this?
  • What good would the newfound humility do for me? My team? My leadership?

You want such a long list that you can't help but feel hope, that despite the worst thing happening, you could be so much better.

Next week, we'll explore 5 more ways to recover from major setbacks. This week, I encourage you to take time to sit and reflect on the major career setbacks in your life. Write out the details, how you felt, how it impacted you, and how your life has looked as a result of it. We'll continue this conversation next week.



Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

How I Learned to Grow by Reduction

How I Learned to Grow byWhen I first started off in counseling, I focused on just one thing: helping male porn addicts get real distance from their addiction.  I expected to focus on that for the rest of my career. As I began to work with male porn addicts, I realized a lot of them had wives, and those wives were really hurting.  So the guys would ask me to meet with them.

I eagerly said Yes.

I then spent time researching how to help the spouse of a porn addict.

I also had to learn how to do marriage counseling.

A friend of mine who was a marriage counselor gave me great tips and strategies for marriage counseling, and I dove right in.

As I continued to work with porn addicts and their wives, they began to share how their kids were being impacted by dad’s addiction.

They asked if I could see their kids.

So I eagerly said Yes.

Then I ran off and studied how to work with kids. I hired a mentor who could give me key pointers on facilitating family counseling.

I then began to work with families who were not dealing with a porn addiction.  So I added family counseling to my list of services.

This went on until eventually I was seeing clients:

  • Who were depressed
  • Who wanted to discover what they are called to do, and how they are designed to do it
  • Who were suicidal
  • Who were traumatized
  • Who were abused
  • Whose loved ones had died
  • Who were addicted to a drug or to alcohol
  • Who struggled with anxiety
  • Etc., etc., etc.

Then, my wife discovered an article on coaching and when she finished, she exclaimed, “Ryan read this!.... This is so you!.... You gotta read this!” I was dismissive of the idea of coaching.  However, after pooh-poohing it for awhile, I eventually read the article.

As usual, my wife was right.

So I called former counseling clients who were ideal for coaching, and many signed up.

In time, I saw the same progression in coaching as I had seen in counseling.  I expanded into life coaching, career coaching, couples coaching, executive coaching, business coaching, coaching on writing business plans, and more.

On the advice of a mentor, I created different sites to emphasize these different disciplines.  I also had multiple email addresses.

Soon, however, this became counter-productive.  I found myself getting mixed up, sending clients in one market a message intended for another market. Understandably, this created some brand confusion.

When it became popular to Google someone’s name before choosing to work with them, clients could see all of the different sites under my name, and brand confusion increased.

I wish I could say that I was consistently hitting home runs in all of these areas. Sadly, however, some were only base hits, and still others were misses.

I wanted to do my best to help them, so I undertook a lot of research, hired experts, and began a trial and error process.  I was putting so much effort in so many different directions that my head was starting to spin.  I did not know what to study next.

In essence, I was not running my practice.  My practice was running me.

The Price of Doing Everything

This took a toll on me emotionally. On a typical day, I went from grief counseling in the first session, to brainstorming on a major initiative with a division leader of a Fortune 500 company, to helping a small business owner learn how to use Google Calendar in the third, to confronting lies that an addict client was trying to sell me in the fourth, and then talking a client down from suicide in the fifth.

My hours got longer.

Yes, my practice was doing well financially, but the personal cost was great.  

I gained a lot of weight, saw my wife and kids less, saw my friends even less (increased isolation is not a good thing for an ENFJ).

Then my coach gave me the book Essentialism by McKeown.  This book teaches that we all need to discover our essential intent, and then we need to put all of our energy into that essential intent.  This leads to much higher productivity, true meaningful success, and fun, all while reducing the amount of decisions you have to make (aka stress).

So what is an essential intent?  “An essential intent, on the other hand, is both inspirational and concrete, both meaningful and measurable.  Done right, an essential intent is one decision that settles one thousand later decisions. It’s like deciding you’re going to become a doctor instead of a lawyer.  One strategic choice eliminates a universe of other options and maps a course for the next five, ten, or even twenty years of your life.  Once the big decision is made, all subsequent decisions come into better focus (Essentialism).”

Discovering my Essential Intent

When I looked at all I did, and I looked at the themes that made the home runs the home runs, I realized what they all had in common:  I was using my gift for getting to the heart.  That is, I was able to help my clients get to the beliefs that fueled their issues.  Once the beliefs were nailed, we developed strategies and plans around those beliefs.  Coaching and counseling clients found true lasting change.  They experienced meaningful success with far fewer burdens than they had before.

To make sure that “getting to the heart” was truly my essential intent, I emailed clients who had experienced home runs through the work we did together, and I asked them, “What is the one thing I do that has been most helpful to you?”  The overwhelming response could be summarized as “getting to the heart." That was great confirmation.

Now that I know my essential intent is “getting to the heart,” my stress levels have come down tremendously.

I have learned graciously to say No to anything that bypasses first getting to the heart --usually by offering the name of someone who could help better than I can.

I have organized all that I do around the theme of getting to the heart, which also means that I am improving that skill.  I am developing a natural strength, and I can’t begin to tell you how cool it is to do what I do best, even better.

I am working fewer hours, accomplishing meaningful goals, making more profit, and beginning to feel like I am finally living.

My coaching clients (and counseling clients, for that matter) are reaching their goals faster than they used to.  They are executing better, in part because we are nailing the root better.

The same thing has happened with the speaking gigs.  When a client says they want to do a workshop on “team building,” I ask better questions, questions that help them get to the heart of what they mean when they say “team building.”  Then I design the workshop around the deepest part of their heart’s desired outcome.

This has led to creating workshops that sizzle now more than they ever have.

I teach my clients the concepts from McKeown's book, Essentialism, and watch them finally attain the work/life balance they’ve wanted. I’ve seen them achieve incredible goals, such as doubling the size of a Fortune 500 division in under four years, and achieving four significant promotions in four years.  Many are reporting to me that their teams are succeeding much better, and with fewer burdens.

How about you?

What is your essential intent?  Here are some questions that might help you discover it:

  • Look at the greatest successes you’ve had. What did they have in common?  What did you do in each of those successes that was similar?
  • What do you naturally do better than others?  How about across time?  What things have you naturally done better across your life?
  • Ask stakeholders, clients, vendors, peers, and others with whom you’ve had home runs:  “What is the one thing I do that has been most helpful to you?”

Chew On This:

  • What would life be like if you were living in your strike zone 80% of the time?

Ryan C. Bailey is an Executive Coach who helps business leaders develop in-demand high performing teams.

*This blog is an amalgamation of a few different clients.  No one single client is being singled out.

Ten Actionable Steps To Facilitating Great Skip-Level Meetings Part 1

10 steFour years ago, a client of mine--let’s call him Bob--received the engagement survey results of the eight teams that directly report to him.  Three teams were at 100% engagement, two teams were at 85% engagement and three other teams had dismal scores, between 30%-40% engagement. Bob tried working with the direct reports of the three lowest teams, to build engagement across their team.  When he realized that the leaders wanted out of their roles, he found better positions for them.

Next, he hired three really talented and hungry managers to take the place of those he had re-positioned.  They worked hard to figure out what to do to increase engagement, and they implemented a strategy.

After about a year, the three new managers received the result of the latest engagement survey.

Guess what happened?

There was NO change in the engagement scores across all 8 teams.

Needless to say, Bob was really concerned about the bottom three, though he was still pleased with the top five.  What could the bottom three be missing?

In an attempt to create an environment in which his direct reports could safely share what was happening, Bob hired me to talk to one of the newer hires, Eva.  Eva shared that her team was being asked to handle far too many calls that were not a part of their original mandate.  “Somehow all of these support calls get dumped on us,” she explained.  “We can’t possibly handle these calls and still meet our goals.  It’s like everyone on the team has two full time jobs.”

I could see that while Eva, the direct report, is still engaged and hungry, those under her are struggling.  So how does my client help those two levels below, while still empowering Eva and the other two managers?

Here are the steps Bob used.  I hope they work for you as well as they worked for him.

  • As the leader, sit down with your manager and get the manager’s buy-in for a Skip-Level Meeting.

It would be easy for the manager to assume that the focus of the Skip-Level Meeting will be to hear all the complaints about her and build a case for her removal.  But a Skip-Level Meeting is NOT about that.

A Skip-Level Meeting is about hearing the perspectives of those closest to the front-lines so that you, as the leader, can best coach the manager.

Make sure that your direct report is comfortable with this meeting and can enthusiastically support it.

  • If you haven’t communicated much with people two levels down, start doing this months before the Skip-Level Meeting is solicited.

In today’s there-isn’t-enough-time-to-do-everything-at-my-job environment, it is not hard to see why a leader may not have much of a relationship with those two levels below them.  Before having a Skip-Level Meeting, walk around, start conversations, create an air of safety, learn about what matters to those employees, whether it is work-related or not, and make sure that the team views you favorably.  This is a critical step.  It will delay the Skip-Level Meeting for weeks, but it is very important.

  • You and the manager send a joint email to the manager’s team.

Co-create a positive and encouraging email detailing why you want to have the Skip-Level Meeting.

Be sure to tell the team what is truly going well, and how you want to make things even better.  Let them know what you are looking to understand.  I would send the questions you are going to ask ahead of time.  See under 5) in Part 2.

In this email, stress that you want to make the meeting as safe a place as possible in order to learn what needs to be learned.  Your aim is to make things run more smoothly so you can better coach the manager for the benefit of everyone, and therefore you will keep everything they say in the strictest of confidence.

No one on the team will know anything that anyone else shared.  Instead, you are going to integrate all the responses from all the meetings, and pull out themes to coach.  Stress that it is important that you know the details so that you can best coach the manager.

  • Create a safe environment

Make sure that the space where the Skip-Level Meeting will take place is free of distractions.  You want to be fully present with the person to whom you are speaking.

Once in the Skip-Level Meeting, reassure the employee that you will not convey anything they share with you to the manager, or to anyone else on the team.  You want them to “let it rip.”  You are far more interested in reaching solutions than in assigning blame for anything that is off.

Stress that you don’t want this meeting to be focused only on the negative. You also want to celebrate what is going well, and find ways to strengthen that.

Recognize something that they do really well, and tell how it impresses you.

Chew On This:

  • What do you most want to find out from those on the front-lines of your business?

*This blog is a compilation of three different clients.  No one particular client is being singled out.