Hiring A Executive Coach? 3 Questions to Ask Yourself (and Your Prospective Coach) First

By Urs Koenig, PhD, MBA, Principal, Redpoint Succession and Leadership Coaching

If you (1) are a coach, (2) have worked with a coach or (3) are hiring a coach (for yourself or others) ask yourself these three questions (discussed in more detail below):

  1. What does success look like and who gets to decide?
  2. What are you paying for (or, if you are the coach, what are you getting paid for)?
  3. What is the process?

(Note, I believe that a lot of what I discuss here also applies to hiring and working with other consultants, not just coaches)

Let’s talk about what most coaching looks like today and what we believe it should look like. Consider the below two scenarios and ask yourself:

  • Which scenario is closer to my experience of coaching?
  • Which scenario is preferable and why?

Scenario I: A senior manager just finished his eight month $35k coaching engagement with a well known executive coach. Although the manager’s boss and the Vice President of Human Resources had a good idea what the manager was working on (he needed to be more assertive and build stronger relationship across departments) they did not participate in the actual coaching process. The coaching was a somewhat mysterious process as it happened behind closed doors. Even some of the coaching client’s close working colleagues did not know that he was working with a leadership coach. Over the duration of the engagement, there were two progress meetings during which the client and the coach reported their progress to his boss and the HR VP. At the end of the engagement, the coach submitted a report in which he outlined how the client progressed during the engagement. He presented primarily self-reported anecdotal evidence. The report included a (positive) self assessment by the client. The coach believed he had earned his $35k fee because he spent a lot of time with the client and strongly felt that the client got better.

Scenario II: A senior manager just finished his eight month $35k coaching engagement with a well known executive coach. The client involved her stakeholders (peers, direct reports, and bosses) from the very start in the coaching process. The client developed her coaching goals (she needed to be more assertive and build stronger relationship across departments) in collaboration her stakeholders and regularly solicited feedback on her progress from them. Halfway through and at the end of the engagement stakeholders rated the client on her progress against her coaching goals in an anonymous online survey online survey. The results of the first online survey were less than stellar and forced the client and her coach to make some changes. The second and final online stakeholder survey showed a significant improvement of the client’s targeted leadership behaviors. The coach collected his $35k fee because (and only because) he facilitated a process by which helped the client get better, as assessed by the client’s 3rd party stakeholders.

Again, ask yourself:

  • Which scenario is closer to my experience of coaching?
  • Which scenario is preferable and why?

A lot of coaching in small business and corporate America is significantly closer to Scenario I than to Scenario II (I know because I have practiced it myself…). For those of you even vaguely familiar with our leadership coaching approach, it will come as no surprise that Lauren and I are strong proponents for moving coaching towards Scenario II.

Let me explain.

I have been coaching for more than 10 years and looking back over this period I am amazed how much the field of coaching and my practice has changed.

I started my coaching as a career coach, quickly transitioned into small business/entrepreneurial coaching and finally ended up finding my calling in leadership (executive) coaching.

I have worked with many wonderful clients (100+ of them) and I believe I have done a lot of good work and, on occasion, some great work. However, I often had the nagging feeling of uneasiness around the measurable impact of my coaching. Yes, the clients felt happy and gave me positive feedback. I did feel they were (for the most part) making good process and got things done they would not have done without our work together. Nevertheless: my outcome driven personality was not satisfied. Questions would linger: How did I really know if I made a difference? Who should be the judge? Did the results achieved justify my fee?

At about the same time I was pondering these questions, Lauren and I were certified in a methodology called Stakeholder Centered Coaching pioneered by executive coaching legend Marshall Goldsmith. In essence, the coach first identifies the client’s key stakeholders (peers, direct reports, and bosses.) Stakeholders are critical to the process as they are people best in a position to: 1) identify the client’s existing leadership shortcomings, 2) give specific and immediate suggestions for ways to improve and 3) assess progress towards desired change. The stakeholders, in essence, are turned into collaborative partners in the coaching process. (Scenario II describes a Stakeholder Centered Coaching engagement, which is the approach Lauren and I now use in our engagements.)

The result? A quantifiable assessment that is hard to “game” by either the coach or the client. (Another side benefit to the Stakeholder Centered approach is that it tends to greatly improve the quality of conversations across the organization, but that’s the subject of another article!)

Coaching represents a big investment in time, money and effort for the client and your organization. Make sure you get a fair return on your investment by asking the questions below before you hire a coach. Does their process look more like Scenario I or II? Does it provide good answers to each of the questions below?

1. What does success look like and who gets to decide?

    • How does the coach define success for the coaching engagement? What about the client? The boss? HR? How is failure defined?
    • How will progress be measured, along the way, and at the end? Is it quantifiable?
    • Who reports progress/results? Is it self-reported (client, coach) or by third parties (e.g. anonymous surveys, stakeholders)

2. What are you paying for (or, if you are the coach, what are you getting paid for)?

    • Are you paying for process/activities (e.g. billable hours spent) or measurable results?
    • Are you having to pay the coaching (consulting) fee no matter what the outcome of the engagement or is the coach’s fee at least partly dependant on the success of the engagement?

3. What is the process?

    • Is the coach able to clearly articulate the process (note: coaching is not (anymore) simply a series of conversations)?
    • Does the coaching only happen in private, behind closed doors, or is the process attempting at building leverage across the organization (e.g. by including various stakeholders)?
    • Is the coaching engagement clearly scoped? Does everyone agree what is being worked on and what is not being worked on? How do you prevent scope creep?
For a detail description of our coaching process, visit our website at Redpoint Coaching.

Effective Managers Say the Same Thing Twice (or More) by Urs Koenig, MBA, PhD, Principal, Redpoint Succession and Leadership Coaching

by Urs Koenig, MBA, PhD, Principal, Redpoint Succession and Leadership Coaching

“If you want something done you need to say it 150 times, seven different ways.”

I must have said this so many times (maybe 150 times) that some of my clients have quoted me back.

I am proud to announce that empirical research (quoted in the 2011 May issue of the Harvard Business Review) is now backing my statement:

”A team lead by Professor Tsedal Neeley (from Harvard) and Professor Paul Leonardi (from Northwestern University) shadowed 13 managers in six companies for more than 250 hours, recording every communication the managers sent and received. The research discovered that one of every seven communication by the mangers was completely redundant with a previous communication using a different technology. They also saw that the managers who were deliberately redundant moved their projects forward faster and more smoothly.”

When the researchers asked the managers if they were surprised about their redundant communication the reaction was this: “Seriously, you think this is interesting? This is how it works. Of course I follow up with yet another message.”

Two key take-aways from this research for you:

  • If you want something done, plan deliberately to communicate the same message several times using different techniques such as instant communication (face to face meetings, calls, Instant messaging) or delayed communication (emails, voice mails).
  • The most powerful way to move the needle on a project or a task is to start with an instant communication (preferable a face-to-face meeting, second best a call) and then follow up with a delayed message (such as an email). The instant communication ensures motivation and buy-in. But the follow up via email is to remind people of their commitments so that it does not fall off the radar screen.
  • Do not use email first (delayed message) and then follow up with a face to face (instant).
For more leadership tips and resources, visit www.redpointcoaching.com.

Leadership 101: Get These Basics Right!

by Urs Koenig, Phd, MBA, Redpoint Succession and Leadership Coaching

Lauren and I absolutely love supporting our clients in getting better. If we could have it our way, our clients would work on their leadership skills all day, every day. Thing is, they have some other things to get done…

Within those resource constraints the question for us is always: which leadership skills, if applied correctly, will make the biggest difference for our clients? Which 20% of behavioral changes will get our clients 80% of the results?

Here are the three basic leadership skills we believe will get you a long way towards the famous 80% of the 80/20 rule:

  1. Valuing being respected more than liked
  2. Transition from ‘Doing’ to ‘Leading’
  3. Owning and managing your own development

Valuing being respected more than being liked

One of my early bosses once told me: “Look Urs, my goal is for you to respect and like me. However, if I can only have one, I take the former.” Because I probably sometimes care more about what other people think about me than I should, this comment has really stuck with me.

To varying levels, we all have the need to be liked. Some of us need less external gratification, others need more. It’s important to understand your ‘default mode’:

  • Are you someone who tends to sacrifice business results in order to preserve a relationship?,  or
  • Do you tend to value business outcomes over the relationship?

Where do you sit on this continuum?

In our experience most leaders fall into the first category: they are leaders who have a strong need to be liked. This becomes a problem when you are fulfilling your need to be liked by comprising sound business decisions. In doing so, you might get a short term ‘like boost’ but in our experience, the same people whom you were trying to please might actually lose respect for you in the long run.

As a true leader:

  • You make the best decision for the organization;
  • You sit down with your people, look them in the eye and explain the business reason for making the hard decision; and
  • You show compassion for those negatively affected by your decision by listening, (really listening!) to their concerns and acknowledging them (including the accompanying feelings).

Transition from ‘Doing’ to ‘Leading’

For many bosses, but especially for founders, it is very comforting to be involved in the ‘doing’ of the day to day of the business. Some leaders I have worked with may be ok to let go of running the operations side of the business but find it very challenging to transition the deep and rich customer relationships they have built over the years.

No matter if it is operations or customer relationships: If you want to grow your business and scale it, you need to transition from doing to leading.

What do I mean by leading?

  • Setting goals for (and with) your people;
  • Getting out of their way so they can do the work they need to do; and
  • Holding them accountable for their results.

Setting goals for (and with) your people

Much has been written about good goal setting. Here is just one piece of advice in order to gain staff buy-in for goals:

  • Have your staff give input on your overall goals for the organization. Don’t just develop them by yourself in your corner office, then present them to staff and expect them to be jazzed about it. Really involve your staff in the development of company goals. Having said that, also be clear that you really want their input but that you will have the final say on what the final goals will be.
  • Once your organizational goals are defined ask your staff: What do you or your team need to achieve in order to get us there? Have them develop their own goals. Make yourself available to provide input and coaching. Having your staff develop their own goals will go miles towards buy-in.
  • Finalize all goals and publish them across the organization. Have everyone know what everyone else is working on. There is no better accountability tool! (Include progress towards the main goals in your staff meetings to help accountability, speed progress, and identify and solve obstacles.)

Get out of the way

Offer your insights, coaching, and resources along the way but don’t give into your urge to jump back in and get your hands dirty. Remember, micromanagement does not scale!

Don’t be afraid to defer to your team member when you get approached by a customer who wants you to personally take care of them. You need to develop your own wording but something along these lines might be a start: “Thanks Jeff for reaching out to me and thank you for doing business with us. Let me put you in touch with my team member, Sherry. She is very knowledgably in the area of xyz and will be a great resource for you.”

It is even better if you have previously brought your key team members along with you to meetings with clients, mentored their client development and relationship skills, and allowed them to develop their own relationships with clients along the way.

Use your co-workers or a coach as an accountability tool to avoid slipping back into old ‘Doing’ habits.

Holding them accountable for their results

One of the most powerful ways to start an accountability discussion is to have your staff self-assess their performance vis-à-vis the goals. If you have hired the right person she will be doing a lot of the work for you. Be sure to celebrate and acknowledge wins (“Lauren, this is a job really well done because of x, y z”) and don’t hesitate to be equally direct where you need to see improvements: “Urs, you know I really value your hard work and this simply is not good enough. In particular I need you to improve x, y, z”). Moving from Doing to Leading can be a very difficult transition to make. You need to redefine your role in the organization and change how you define your success.  A good day is no longer about how much YOU did but about what your TEAM achieved. 

Owning and managing your own leadership development

Hint: no one else will own and manage your leadership development if you won’t, so here is where micro management can work well for you.J

To kick the process off, here are some questions to ask yourself:

  • When was the last time you invited the people you work for and with to give you their honest feedback on how you are doing as a leader? What is holding you back from doing it in 2011? What are you afraid to hear?

How clear are you about the leadership skills needed to take your organization to the next level? Do you have them? If not, do you have the potential to acquire them? If yes, how will you go about it? (see below)

  • How much formal and informal work on your leadership skills have you done in 2010? What are you planning to do in 2011? (This may include: formal training, consciously taking on new stretch assignments on the job, coaching, mentoring, and participating in a peer group).

Reflect on your answers to the above questions and then answer the following simple question:

What one thing are you willing to commit to in 2011 to become a more effective leader to help you get the basics right? 

We would love to read your response to this question. Send us a 10 pager or a one liner to: changeability@redpointcoaching.com. Your entry will go into the drawing for one Leadership style assessment valued at $100 and 5 Starbucks coffee cards. We will also publish all entries (anonymously, of course) over the course of the next few ChangeAbility ezines.

Develop Trust and Devote Quality Time: Two Ingrediants of Great Leadership

I’ve recently conducted several 360 degree surveys for my Redpoint clients. A 360 degree survey provides feedback to a business owner in the form of an anonymous performance assessment by all the people (subordinates, colleagues, managers, clients, suppliers) who surround that person (hence “360 degree”).

In the case of my clients, the owners and CEOs typically want to receive feedback on their leadership skills from their staff. During the process, we define the criteria they want to use for the assessment, and then I draft a questionnaire, survey the staff, and compile and present the results.

Now, if you think this is an intimidating exercise, you are not alone! Because of the anonymous nature of the exercise, staff members are often brutally honest and are not reluctant to reveal their views. In each case, my clients have taken on the challenge bravely, knowing that this candid assessment is a critical first step towards their own improvement.

Back comes great feedback about their performances as “the boss.” They are perceived as exceptional at interacting with clients, great at getting business results and strong communicators. The two critical areas of improvement I continually observe are:

  • Lack of quality time spent with staff; and
  • Lack of trust

Critical area #1: You need to spend more quality time with your staff

Lots of owners of growing companies experience this: heavy workloads prevent you from spending time with the very people you rely on to get the job done, and who look to you for direction, mentorship and reward. Your busy schedule therefore leads to ‘seagull’ management: you stop in quickly and drop a ton of information, directions and sometimes criticism on your staff before you quickly take off again.

It came back loud and clear from my clients’ feedback: you need to take the time to talk to people substantively, ask them how things are really going, and really listen to their answers. It is not necessarily the quantity, but quality of time and interaction that counts.

Staff members who have been heard and feel that their feedback and suggestions have been taken on board are always more engaged workers. And engaged workers are almost always better performers.

Ask yourself: Over the last week, how many people in my business have I asked how things are going? How many people have I thanked for a job well done? Remember: praise in public, criticize in private. And, of course: when you are wrong (and you are and will be :-), apologize.

Critical area #2: Lack of trust: “We sometimes feel you do not trust us. It always has to go your way”

I am sure this sounds at least somewhat familiar to most business owners. After all, this is your baby, you have grown it and you know best what it needs. Trusting someone else to take over and perform tasks you have owned for so long is incredibly difficult.

In fact, the reason why people start businesses in the first place is that they believe they can perform a particular task better than anyone else (or at least better than their current or past employer). This strong belief in one’s abilities is one of the great strengths of the entrepreneur. Yet we know this strength can also become your biggest liability: the reality is that if you want to build a company, you have to trust people to help run it for you.

Trust sounds like a challenging concept to actively develop, but Carl Robinson, a Seattle based psychologist and executive coach, offers some helpful insights in his discussion of trust that appeared in an article in the Journal of Managerial Psychology (2004):

Motive-Based Trust is what most people think about when they think of trust. It is based on the belief that another’s values, goals and beliefs are closely aligned with yours.

Competency-Based Trust is based on your belief that your employees have the capabilities to get the job done.

So how then can we learn to develop these forms of trust?

How To Develop Competency-Based Trust

  • Assess Your Hiring: Do you have the right people in place to get the job done? Do they either have the necessary capabilities or are they willing and able to learn them? If yes, read on. If no, you need to consider making some staff replacements.
  • Take time to observe your people in action. Give them goals and let them come up with their own methodologies. Resist the huge temptation to jump in with solutions and advice-giving. If, after a while, you do not like what you see, go back to assessing your hiring practices or start providing more training.
  • Look for outside support. Hire a coach or consultant and/or establish a board you can lean on to help assess candidates. For more info on the benefits and how-to’s of establishing a board see: http://www.redpointcoaching.com/resources/documents/Oct03.pdf .

How to Develop Motive-Based Trust

While developing competency-based trust is relatively straightforward, motive-based trust tends to develop only once competency-based trust is established; motive-based trust is, therefore, harder to assess. Because this is a more intangible area, lots of entrepreneurs rely on their instincts. Remember, though, that you have great tools to align motives:

Remunerate staff based on their performance (e.g. a commission pay structure for your sales staff or a profit sharing pay scheme).

  • Provide key staff members with equity in your business. Carl Robinson argues that in an imperfect world where trusting relationships sometimes have to develop quickly, distributing equity is a great way to establish tentative trust.

My experience with 360 degree surveys has shown me that spending quality time with your staff and developing competency- and motive-based trust makes all the difference between mediocre and great business owners.

Contact me if you would like more information on conducting a 360 degree in your organization.

How To Lead Generation Y: Delivering The Leadership That Will Make Them Thrive Is Easier Than You Think

by Urs Koenig, PhD, MBA

Personal note: In my previous position as marketing director at Merriman, a financial advising firm, I had both the two oldest (60+) and the youngest member (23) of the entire firm on my team. My team spanned almost all four of the previous generations (Traditionalists, born between 1926-1938), Baby Boomers (1945-1960), Generation X (1961-1981), and Generation Y (1985-1995). Including an intern, I had four Generation Y members working for me. One of the things I enjoyed most about my job was to facilitate and lead intergenerational team-work. If you are leading young adults (or are in charge of people who lead them) I believe you will find the lessons I have learned about leading members of Generation Y helpful.

Shannon is 25 years old. She is in her second job out of college. She was hired as a ‘high potential’ candidate by her current company. She survived several rounds of layoffs and is very unhappy in her current position. Her old-school, corporate, generation-X boss micromanages her time while not providing much feedback or guidance on her actual job. Shannon is disillusioned with management and cynical about her job. She puts in the absolute minimum in time and effort and spends a lot of her working time surfing the web. The poor job market is the only thing stopping her from leaving the company.

Bruce is 19 years old and in his second year of college. He is the third generation in a family business. His grandfather (70) only recently handed over day-to-day operations to his father (45). This summer Bruce is interning as the ‘social media guru,’ his first paying job in the family business. After a few weeks, he is highly frustrated. In his view, people at the company simply ‘don’t get it.’ He truly desires to make an impact and help make a difference but feels that no one is listening to his ideas or values his input. In the interest of family peace, he decides to continue with the internship but secretly vows to never again work in this family business.

The above real-life examples demonstrates what happens when Generation Y leadership goes bad.

Today’s young adults entering the workforce are a different breed than those of any of the generations before them. They must be lead slightly differently as they enter the workforce:

Provide constant feedback (and manage their sense of entitlement)
These young adults are used to and crave instant and constant feedback. Most of them grew up with lots of praise. Many Trophy Kids received ribbons and trophies simply for showing up at Saturday games. Their parents have told them over and over again they can achieve anything they want. They are highly optimistic and sometimes out of touch with reality. They are definitely not used to being told that the quality of their work needs improvement.

As their leader, it is virtually impossible for you to over communicate. Provide them with ongoing, just-in-time feedback. Give them the praise and appreciation they crave. At the same time, hold them accountable. You might be the first one to ever tell them the truth about the quality of their work. If they are falling short, you need to tell them. As their leader and mentor, you need to help them discover their weaknesses and strengths and then play to those strengths

A word of caution though: Don’t ever micro manage their time. Instead, lead by objective. They value a flexible schedule and might do their best work from the local Starbucks or at 2 a.m. in their pajamas. Assess their performance, not their attendance!

Be a strong mentor and coach
This is probably the most important lesson of them all. Members of Generation Y are extremely responsive to mentoring and coaching. Develop strong and meaningful relationships with them by really getting to know them: Take them for coffee, go for a lunchtime walk/run, play some golf and most important, ask questions and really listen to what they have to say.

Learn their passions, their desires, their aspiration in life. In return, share your experiences and lessons you have learned. They are hungry for your insights, they love to be ‘in the know’ and they will soak up your knowledge, feedback and advice. Become their strong mentor and coach and your Gen Y’s will thrive, blossom and follow you loyally.

You might also explore a ‘reversed mentoring’ approach, something Jack Welch at GE pioneered over 20 year ago. The idea is to pair Baby boomers with members of Generation Y. The Boomers share their work experience while the Generation Y team members enlighten Boomers about new technologies and social networking.

Share why their work is important
These young people have little time for doing things because they are told to do so or because ‘that’s how we have always done it.’ They are hungry for data and information. Remember that, for better or worse, many of them are constantly multi-tasking, and are taking in thousands of technology messages every day. Faced with this overload, they quickly sort incoming information between what they deem is ‘need to know’ versus ‘nice to know’.

Provide them with lots of context and information. Communicate the importance of their work and tell them how it fits into the company’s overall big picture. Help them see that what they do really matters. Show them how their work is making your organization better, making a difference in the world and is part of something bigger – not just adding to the bottom line. Several studies, for example, have shown the importance of environmental causes for Generation Y.

In short: get them fired up for your vision, show them how their work will directly help you to make the vision a reality and your Gen Y-ers will be the best people who ever worked for you!

Give them opportunity for input and ownership
Members of Generation Y have been on their laptops since they were four. They grew up with posting and voting on Facebook and blogs. They have a strong desire to express themselves, to comment and to provide input on topics.

Be bold and have them provide you input and feedback on high-level strategic topics which you would normally not share with them. They will forever value you for giving them the opportunity to ‘upload their thoughts’ and much like any generation before them, they will throw their support behind what they helped to create.

After they have given you their input, it’s time to challenge them: Carve out a project with a clearly defined deliverable, a budget and a timeline, then give them full ownership of it. Make yourself available as a coach and mentor. But don’t micromanage them or their projects.

Be tough when assessing the results of their work by providing the honest, credible feedback they so crave.

Are You Ready for Succession? Tackling the personal challenges of handing over leadership

By Urs Koenig, PhD, MBA www.redpointcoaching.com


The technical aspects of succession planning are covered at length in both the academic literature and in the work of ‘real life’ consultants. Less explored are the very real and equally influential personal struggles and strong emotions that often unfold during the succession process.

Anyone who has ever been in charge of an organization knows the kind of personal investment this work requires. After a while, being the CEO is not what you do but who you are. This is even more true for founders. So transitioning out of the top spot and handing over the role that has essentially become ‘You’ is a very personal process indeed.

Even as you continue to lead your organization, you need to prepare for your departure. You might think that this will be easy. You will likely be wrong! Handing over leadership to the next generation will be tougher than you think.

Letting go is hard to do
Any successful transition starts with coming to terms with the fact that it is probably going to be hard for you to let go. Leaders who realistically face the personal challenges of transitions are much better prepared to leave than those who deny the difficulties.

In addition to leaving significant monetary benefits and perks behind, what makes it so hard to leave what is after all a highly stressful job. What can you do to ease the transition?

The mind-set that served you well going into the job (or founding the company) will make it challenging for you to transition out–in all likelihood, you have become the job. Going into the job you had to be convinced that you were the one who could do the best job at leading the organization. You also must have either convinced a board and/or numerous lenders and investors that you were the absolute perfect person for the job. For most leaders, pulling this off requires a very healthy ego when it comes to work performance. Even if you are modest and not a show-off, transitioning from being in the midst of it all, making it all happen, to taking a background mentoring role and getting your kicks out of your successors’ successes (versus your own) can be very challenging.

Along with the proverbial corner office, here’s what you’re likely to miss most:

Status: When we hear status, we often think of corporate CEOs with all their perks, name recognition and corporate jets. But status can come in a lot of different forms. Successful business owners in small town America, for example, enjoy a fair share of status as well. They are admired by their community and receive a lot of recognition for their position. Even if you were never seeking status, losing it and becoming a ‘used to be’ can be very difficult. Many studies have shown that losing something (e.g., status) creates significantly more pain than the amount of pleasure we enjoyed when we originally obtained it.

Power: When you’re in charge, you know your job matters! Every single day you are making a difference in people’s lives. Not many people have as much influence as you. Power might simply be defined as being able to influence. No one in any managerial position gets anything done without power. Top leaders have a high need for power. Throughout your career you have gradually gained more and more power. When you leave your job you will suddenly feel a loss of power. Marshall Goldsmith recounts one executive’s perspective: “It was like falling off a cliff. My loss of power: ‘They are not bothering to return my phone calls.’ When I was the CEO, my phone calls always were immediately returned!”

Meaning: Most CEOs find true meaning in their work. They truly care about what their organization is doing for their clients. They value their workforce and are passionate about the mission of the business. You might fear that nothing you will do in the future do will ever make as much of a difference and create as much meaning for you as being CEO. You might be right. Often one of the most challenging parts of the succession process is to find new and uncharted ways to create meaning in your life.

Relationships: Unless you are working in a family business, you will have spent significantly more time with your co-workers, clients and suppliers than with your friends and family. As the leader, you like most of your co-workers – otherwise they would not be working for you anymore. You have been through highs and lows and have seen the best and worst in each other. The more you have been through together the closer you will be. Some of your co-workers will have become close friends and some feel like family. It can be very hard to leave your workplace friends and family. 

Picking the Right Time
It will almost certainly be hard for you to choose the right time to slow down and hand over leadership. If your organization is achieving wonderful things, growing, making a difference for more people every year, adding cash to the bottom line and providing a wonderful work environment, why in the world would you want to leave?

If, on the other hand, you are falling behind or not achieving what you set out to do, your competitive drive won’t let you quit. After all, a lot of what you achieved was due to the fact that you kept going against all odds. You persevered when a lot of other people would have thrown in the towel. You will be convinced that you will be able to turn the ship around if only you are given a bit more time.

When deciding on the right time to leave, consider these two useful principles:

  • You make the call – leave while you can still make the decision rather than having the decision made for you. Remember that being able to choose the right time to leave is a privilege. Many leaders are not that lucky. They either get pushed out of their position (by the board, other family members, or their successor) or their health forces them to step down. Treat this choice as the privilege it is and don’t simply bury your head in denial about your eventual departure.
  • Go when you feel pulled towards something rather than when you feel pushed out of the business – While it will be difficult to leave your current position, try to make the move at least in part because you have ‘something better’ to do afterwards. Move while you are attracted to and intrigued by (and in demand for!) a different opportunity and before you are pushed out of your leadership position either by higher forces or by the fact that you have tired of the top job.

Building a Great Rest of Your Life
‘Who am I going to be?’ and ‘What am I going to do?’ are the all-important questions you have to ask yourself as you prepare for succession.

Most retiring leaders leave their positions in their sixties when they are in good health and have twenty + years ahead of them. For the majority, a leisurely retirement spent sampling cruises and chipping away at their golf handicap is not an option. Many have tried it. Most realize that the desire to just rest and relax won’t last very long and that their drive and ambition did not simply disappear with their job. Simply stopping might therefore not be an option.

Today’s retiring leaders are looking to continue to make a contribution and pursue something that has true meaning. Instead of becoming a person who used to make a difference, they want to remain a person who still is making a difference.

They are also looking for happiness realized by living lives full of meaning and contribution, and enjoying close relationships with friends, family and the new team members in the ‘after job.’

If you are nearing succession, think about the rest of your life. Now is a great time to start planning and challenging yourself. How can you make a contribution? What makes you really happy? How can you find meaning?

You might have 20-30 years left. How can you make this time count for yourself and for the people around you?

If you have a path beyond your current leadership role that you believe will give you meaning and make you happy, it will be much easier for you to let go. If on the other hand, you see no options that excite you, you are more likely to hang on much longer than you should.

Three concrete things we encourage our clients to do when we’re coaching them through handing over the baton of leadership of their business:

  • Learn from others who have been in your shoes. Seek out peers who have gone through the process. Find out what has worked for them and what has not. Remember: a smart person learns from her mistakes. An even smarter person learns from the mistakes of others.
  • ‘Interview’ the people who know you best about potential pitfalls and opportunities of the succession process. Treat this as a research project: What do your friends and family think? What are they most excited and most worried about for you? If they could give you once piece of advice, what would it be?
  • In thinking about how to build a great rest of your life, fast-forward 5 years and write a holiday letter for 2015 to your friends and family. What did your life look like this year? How did you spend your time? What got you excited? What were the challenges? What are you looking forward to in 2016?

Note: this article was inspired by the writing of Marshall Goldsmith, in particular his book: Succession. Are You Ready? Harvard Business Press 2009.