The Art of Strengths Coaching

S is for Satisfying Work And Squiggly Careers  

There are many ways to develop a satisfying career. One approach is to follow a specific profession and follow a relatively straight career path. Certainly this is a path that is followed by many people.

Some people pursue squiggly careers, however, where they move from project to project and role to role. Sometimes the projects and roles they do can appear quite different.

People who have squiggly careers often pursue two themes. They aim to follow specific principles they believe in and do satisfying work. They express this approach by doing various projects and roles that are satisfying.

Mitch Joel talked about this concept in his book CTRL ALT Delete. Here is a short introduction to his view of squiggly careers. You can discover more about his work on various topics via the following link.

 Embrace The Squiggle

In the second half of the book (called Reboot: You), I talk about the value of having a squiggly career.

How the most interesting and successful people I know didn’t have a very linear trajectory.

How it will not be uncommon for many of us to have 4-5 different careers in our lifetime (as opposed to 4-5 different jobs in our careers).

Too many people feel trapped and compelled to stay the course. Too many people think that a linear career is the prudent and true path.

Squiggly is interesting. Squiggly is better.

Looking around, can you think of somebody who has followed this approach? What have been the roles or projects they have done in such a squiggly career? This could be somebody you know or somebody you have heard about.

The person may have started out in one profession but is now do something that appears quite different. Or they may have moved from project to project in several different fields. They may have moved from nursing to hospitality to running a café to running their own business or whatever.

The things they have done may not appear to have much in common. Looking at these, however, can you see any recurring themes? They may have involved encouraging people, creating enriching environments, building new things or whatever.

If you wish, try tackling the exercise on this theme. This invites you to do the following things.

Describe a person who has had what appears to be a squiggly career.

Describe the specific jobs or projects they have done that make it look like they have had such a career.

Describe the specific common themes in some of these jobs or projects.

Geoff is somebody who has had such a career. One of his common themes has been focusing how to make things work better. This later expressed itself in helping people to fulfill their potential.

A promising young athlete, he suffered a severe injury during his teens. The recovery process was long, but it fuelled his interest in studying how the human body has the capacity for healing.

Geoff studied a science subject at college, but he found himself gravitating towards coaching young athletes in the local schools. At that stage he thought of going on to teach physical education. But the first job he got was something totally different.

Visiting a career fair, he was attracted to a software company that helped organisations to be more effective. The salary was also enticing and would give him some independence. Starting as a trainee, he soon moved on to visiting customers to install the software.

The customers began asking him to solve certain problems. Geoff proved to be good at getting to the heart of the matter and making thing work effectively. He began building a network of good relationships with customers.

Spotting this talent, his company asked him to move into sales. Reluctant at first, Geoff redefined the role as helping customers to succeed. This resulted in him landing several big contracts and eventually leading the sales team.

Around the same time Geoff rekindled his interest in sports. Backed by his company, he helped to develop software that athletes could use to improve their performance. This led to him taking a qualification in sports science.

Serendipity then took over. Meeting a former boss at a conference, Geoff was invited to lead an intrapreneurship programme for their company. Like many such initiatives, it was inspired by the work of Art Fry, the inventor of Post-it Notes at 3M.

The intrapreneur approach encouraged individuals to develop new products and services whilst remaining as paid employees. The company did not want to lose talented people, so it provided a platform for them to implement their ideas.

Geoff stayed in the role for five years. The programme produced some notable successes but then ran into trouble. The leader who hired him moved on and the new leader embarked on cost cutting. Fed up with fighting the system, Geoff looked for other opportunities.

At this point he contacted me through a friend. Bearing in mind his overall life goals, we looked at how he could find or create satisfying work. We focused on how he could continue:

To build on his strengths.

To find sponsors – employers or customers – who would pay him for what he did best. 

To help these sponsors to achieve success.

If you are interested, you can discover more about this approach via the following link.

Satisfying Work

Geoff then looked at his options. He could try to find a full-time role, do freelance work or build a small business with some former colleagues. Choosing to go the freelance route, he aimed to do project work where he could deliver something substantial to customers.

Bearing in mind that Geoff’s network would be the most likely place to find work, we began exploring possibilities. This led to him doing the classic exercise Find A Need And Fill It. Looking at the people he knew, Geoff focused on the following things.

The needs they may have at the moment.

The needs they may have in the future.

The specific things he could do to use his strengths to fulfil these needs. 

Geoff clarified the specific results he could deliver for several people in his network. These included several of his former bosses. He then began meeting these people for informal chats.

After the first few minutes of these meetings, he asked about some of the challenges facing their organisations. Geoff then shared practical ideas they might use to tackle the challenges.

He aimed to do five such meetings a week. These eventually led to him leading two projects. One was a talent management programme. The other involved building a prototype for delivering better customer service and producing success stories.

Geoff now works as a trusted advisor to both business and sports organisations. He helps people and teams to deliver high performance.

Because of his background, Geoff goes beyond talking about concepts. He gives people practical tools they can use to fulfil their potential. This has been a theme throughout his squiggly career.

Different people do many different jobs when pursuing such careers. One key factor, however, is that they purse the theme of doing satisfying work. This can take them to many different places during their careers.

Looking at your own life, what are the kinds of work that you find satisfying to do? You may enjoy developing technology, helping customers to succeed, nurturing future leaders, designing beautiful things, giving people hope or whatever. How can you do this satisfying work in the future?

One person I worked with found her present role this way. When going for interviews, she was often asked the old career questions:

“What are your career aspirations? Where do you want to be in five years time?”

She answered in the following way.

“The world of work is changing rapidly, so I cannot tell you exactly what the role will be. Whatever the role is it, however, it will have the following qualities. It will be one where:

1) I am working with a company that is developing pioneering technology.

2) The technology helps people to take more control of their lives.

3) I have the opportunity to develop future leaders for the company.

“I will then do my best to help the company to achieve ongoing success.”

You will, of course, have your own approach to finding or creating satisfying work. The way you express this could lead to you developing a straight line or squiggly career.

If you wish, try tackling the final exercise on this theme. This invites you to do the following things.

Describe the specific kinds of work that you find satisfying to do. 

Describe the specific things you can do to find or create such satisfying work – such as by doing certain kinds of projects or jobs – in the future.

Describe the specific benefits – both for yourself and for the people you work for – of doing such satisfying work.


    L is for Leaders Showing Love rather than Just Working Through Lists

    There are many models for providing good leadership. Some leaders go beyond providing direction. They also show love rather than just working through lists of tasks.

    Good leaders often create a positive environment in which people feel motivated to do their best. They show love in different ways.

    They act as positive models by being warm, kind and encouraging. 

    They encourage people to play to their strengths.

    They show love for the particular mission and inspire others to want to achieve the mission. 

    They show respect for people by working through the right kinds of lists – such as managing by outcomes rather than managing by tasks.

    They share success stories that highlight the superb work people are doing to achieve the picture of success.

    Looking back, can you think of a leader who showed love rather than just focused on lists? They may have been a teacher, coach, manager or other leader who encouraged people. They may have been somebody you knew or somebody you have heard about.

    Such a leader may have acted as a positive model by being warm and kind. They may have reached people’s hearts as well as their heads. They may have transmitted belief in a compelling mission and inspired people to want to achieve the goals.

    If you wish, try tackling the exercise on this theme. This invites you to do the following things.

    Describe a leader who you believe showed love.

    Describe the specific things they did to show love. 

    Describe the specific things that happened as a result of them taking these steps.

    As mentioned earlier, there are many models for leadership. Let’s explore some of the steps that good leaders take to show love rather than just focusing on lists. They often start by demonstrating the basics of leadership.

    Good leaders
    provide direction

    Good leaders communicate the team’s purpose, principles and picture of success. They then give people to chance to decide if they want to contribute towards achieving the goals.

    Different leaders do this in different ways. Whichever approach they use, they often communicate the What, Why, How, Who and When. Here is an overview of some steps they take to provide direction.

    Good leaders act
    as positive models

    Good leaders aim to build a positive culture in which motivated people can achieve peak performance. How to make this happen?

    They recognise that they are always on stage. People will watch what they do rather than what they say. Bearing this in mind, they aim to act as positive models.

    Gill was a leader I worked with who took this approach. She explained this in the following way.

    “My main job is to keep telling people the team’s story. It is then to give them the support they need to deliver their part of the strategy.

    “When walking around the office I realise that I am on stage. So it is important for me to be open, approachable and take a sincere interest in people.

    “This is something I learned from one of my old bosses. Whenever we met, he made me feel the centre of his world. He asked about the work I was doing and if there was any support I needed.

    “Five years ago I moved from running a team of 40 to taking over our European business. It was important to show respect to people. So I spent the first two months travelling to Rome, Madrid, Stockholm, Berlin and the other offices.

    “People seemed a bit anxious about my visits, but I tried to put them at ease. I asked about their previous successes and the challenges facing their parts of the company.

    “Certainly I had a clear vision for the European business, but I also wanted to connect with people in the different countries. My predecessor had not bothered. He simply told people they had failed and he was going to show them how to run a business.

    “Two months after arriving I gathered everybody together to present the team’s story, strategy and picture of success. During the presentation I referred to some of the ideas people had shared during our meetings.

    ‘People understood it wasn’t a democracy. But they enjoyed seeing their influence on the vision.”

    Good leaders encourage people
    to build on their strengths

    Good leaders care for the team’s mission and also care for their people. They aim to get a win-win for the team and for the individuals. How to make this happen?

    One approach is to communicate the team’s specific goal. It is then to encourage people to build on their strengths and make their best contributions towards achieving the goal. Peter Drucker supported this approach. He wrote:

    The task of leadership is to create an alignment of strengths in ways that make the system’s weaknesses irrelevant.

    Good leaders take certain steps to co-ordinate people’s strengths. They do this by focusing on the following themes.

    Good leaders show
    love for the mission 

    Good leaders communicate a compelling mission and also inspire others to want to achieve the goal. They embody many of the elements described by Robert Greenleaf in his book Servant Leadership.

    He had a profound effect on helping people to see the leader’s role as that of servant. Different people have different motivations for becoming such a leader, but Robert explained that:

    It begins with the natural feeling that one wants to serve, to serve first. Then conscious choice brings one to aspire to lead …

    Great leaders often see themselves as serving something greater than themselves. This could be a purpose, mission or other kind of cause.

    Some see themselves as serving the vocation they aim to follow. Such causes often aim to enable human beings to flourish.

    Such leaders may want to serve the cause of civil rights, freedom, justice, building a better future or whatever. They often aim to build a more caring society.

    This approach also stretches into other fields. Donovan Campbell, author of The Leader’s Code, a U.S. Marine Corps veteran wrote:

    So what does the military really teach about leadership? Put simply, it teaches a servant-leadership model.

    In simplest terms, servant-leadership teaches that a leader exists to serve a mission first, their teams second, and themselves a distant third. Leaders understand what they are doing and why they are doing it.

    Such leaders have a strong will. They focus on serving the work and the people who want to serve the mission, however, rather than their own self-interest. So they may go the following route.

    They choose to serve something greater themselves – such as a cause.

    They attract people who also want to serve the cause.

    They encourage and enable the people to succeed in serving the cause.

    Ken Blanchard explains his view of such leadership in the video below. You can discover more about this approach at the website devoted to Robert Greenleaf’s work.

    Good leaders manage by
    outcomes rather than by tasks

    Good leaders show respect for people by managing by outcomes rather than by managing by tasks. They do this on both a team and individual level.

    Such leaders enable their people to deliver their goods. They therefore do, when appropriate, work through lists. These are the right kinds of lists, however, that focus on outcomes rather than detailed tasks.

    Such leaders are the polar opposite of old style leaders in retail who ran intimidating meetings on Monday morning. Poised with a detailed list about what went wrong the previous week, they cross-examined each person.

    These leaders then drilled deeper. They sometimes put people on the spot to describe their detailed list of tasks for the next week. People dreaded the meetings. They sat there wondering if it would be their turn next.

    Good leaders take a different approach. They invite people to look at the big picture and focus on the outcomes to achieve. They often go through the following steps.

    Gill, who I mentioned earlier, uses this approach. When faced by a difficult customer situation, for example, she invited her team to explore the following questions.

    “What are the outcomes we want to achieve in the short, medium and long-term? What can we do to get wins for our company, the customer and our colleagues? How can we get a win-win-win?”

    She also used the outcomes approach when inviting people to clarify the best contributions. This could be challenging, because many people were used to writing lists of tasks. They described what they were going to do rather than what they were going to deliver.

    Gill spent a lot of time with each person making crystal-clear contracts about the real results they would deliver. Each person wrote their aims under the headings of profits, products and people. Here is an example of one person’s goals that were written in outcome terms.

    My Contribution Towards
    Achieving The Picture of Success


    To ensure my team achieves its financial targets – a profit of £500k.

    To develop 3 new customers and do work with them that delivers a profit of £100k.

    To reduce our overheads by £100k.


    To ensure more than 90%+ of our customers say they are extremely satisfied with our work.

    To develop 2 new products and pilot these successfully with customers – then launch these products by the end of the year.

    To simplify 2 of our complex products to ensure these are more user friendly for customers – then get a further £100k’s worth of orders for these before the end of the year.


    To deliver an internal morale rating of 90%+ of our team members saying they enjoy coming to work each day.

    To educate, equip and enable 2 of my team members to win promotion and move on to other roles in the company.

    To recruit 4 new positive team members who take responsibility, build on their strengths and get some early successes that contribute towards achieving the team’s goals.

    The person then met with Gill every month. They started by revisiting the agreed outcomes and then describing the following things.

    The specific things they had delivered in the past month towards achieving the goals.

    The specific things they aimed to deliver in the next month towards achieving the goals.

    The support they would like and any other topics they would like to discuss on the road towards achieving the goals.

    Gill created an encouraging environment in which people felt able to discuss their successes and challenges. She kept focusing on outcomes to achieve rather than falling into supervising the person’s tasks.

    Good leaders
    share success stories

    Good leaders show love for the organisation they are leading by continually producing success stories. They keep showing what good looks like. They keep highlighting the following things.

    The specific times when people have performed brilliantly.

    The specific things people did right then – the principles they followed – to perform brilliantly. 

    The specific things people can do to follow these principles – plus maybe add other skills – to perform brilliantly in the future.

    Different people use different frameworks for sharing success stories and showing what good looks like. Below is one framework.

    People start by choosing a title for the story. They then describe the specific situation they encountered. They could be helping a client, solving a problem, making internal processes work better or whatever. They describe the challenges they faced and the desired picture of success.

    People move on to describing the key strategies they employed to tackle the issue. They describe the results that were delivered to achieve the picture of success. They then summarise what was learned from the experience. They describe:

    The specific things that worked and how they can follow these principles more in the future. 

    The specific things they could do better next time and how. 

    The specific other things of interest that emerged.

    Good leaders encourage their people to embrace the ethic of constant improvement. One approach is to start by publishing success stories. People are then more likely to grow in confidence and develop the strength to tackle other challenges.

    There are many models for leadership. One approach is to provide direction and show love. It is then to, when appropriate, work through the right kind of lists, such as those that focus on outcomes rather than tasks.

    Imagine that you lead a team. What do you do well when focusing on leadership, showing love and working through lists? What could you do better and how?

    If you wish, try tackling the exercise on this theme. This invites you to do the following things.

    Describe the ratings you would give yourself in the areas of providing leadership, showing love and working through the right kinds of lists.

    Describe the specific things you can do to maintain or improve the ratings in each area.


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