The 5 Thinking Hats of Transitions: What they are, how to use them, and how they benefit any transition


I believe thinking is a skill and can be improved with the right help, frameworks, and methods to do so.  In a transition, according to author Nancy Schlossberg of Retire Smart, Retire Happy: Finding Your True Path in Life, there are five common ways people explore their retirement and the next stage of life in this important transition.  I'm taking this a step further and extending this idea into ALL Transitions as well as coupling it with some of famous creative thinking polymath Edward de Bono's thoughts (he's also a psychologist, philosopher, author, inventor, and consultant) from his book Six Thinking Hats.  The benefits of trying on each hat when thinking about, planning, or experiencing a transition may help to reframe, reorganize, or reinvigorate what the art of the possible is for you.  Ultimately, this will enrich your transition whether it's retirement, a career change, or even in an organizations transition in a larger sense.

The 5 Thinking Hats of Transitions

These 5 thinking hats are presented here in no particular order or importance.  Think of them as general ways people experience and explore a transition and that one does not necessarily experience one at a time.  More often then not, we traverse a mixture of these types at any given time or we "wear multiple hats" at the same time.  However, if you stop and think with a particular "hat" on and perhaps even pursue your transition fully embracing a particular "hat", you may find the experience more rewarding, enriching, simplified, and straightforward.  

  1. The Continuer
    1. This hat is simply an extension of your current identity or organizations identity.  It seeks to perpetuate the roles, relationships, routines, and assumptions that make up your work, home, or volunteer life and they remain central to who you are and what you find important.  This mindset can sometimes be more possible in one circumstance vs. another.  Perhaps you can move from a full time teacher to a retired teacher but a volunteer in the same school or school district, thus maintaining almost similar structure to your life. 
    2. Questions to explore:
      1. Can you continue your current identity and life structure but packaged in a different way or ways?
      2. Are there opportunities to maintain same or similar roles, routines, relationships, and assumptions post-transition?
      3. What are the pros/cons with this frame of mind and pursuit in your transition or your organizations transition?
  2. The Searcher
    1. With this hat on, you understand and act with the knowledge that you need to move on and transition to something new but you're unclear about the exact place you're seeking or going to end up.  There is space with this mindset for trial and error to gravitate to what fits best.  The key with this hat is to focus on perseverance to move through the transition and end up where desired.
    2. Questions:
      1. What are a few steps you can take to seek out new roles, relationships, routines, and assumptions for your next stage after you transition?
      2. Are you comfortable trying something new and dropping it if it doesn't suit you?
      3. What kinds of activities and resources might be required by you or your organization and spend some time exploring, searching, and experimenting?
  3. The Retreater
    1. This mindset happens to many of us at some point in our life, in some kinds of transitions.  Basically, its like giving up, and succumbing to the minimum level of roles, relationships, and routines in life.  Boredom or in some cases, depression, characterize this hat.  I believe this can be an important stage of transition as well as thinking about an upcoming one because it can be thought of as stripping away all distractions, complexities, and unnecessary aspects of your life or organization.  The adage "no where to go but up" exemplifies the realization of this perspective.
    2. Questions:
      1. What might happen if you "gave up" and stopped being deliberate, planning, and pursuing something new and different for your transition?
      2. What kinds of disabilities, ailments, or challenges might occur for you to become a true Retreater in your next transition?  How could you reframe these circumstances to step out and away from a Retreater mindset?
      3. What would it look like for your organization to put a stop to it's current initiatives and pursuits of growth (but still serve your customers well) and instead allow space to settle back and simplify for some amount of time?
        1. How would this benefit your organization? Harm your organization?
  4. The Adventurer
    1. This is a mindset of full of positive and new "what if's?" What if you stepped out of your comfort zone and learned a new athletic skill? Art skill? What about a whole new capability set for your organization like in-depth sales and customer service training for your whole organization? This is the "go big or go home" mindset.  I look at these transitions as taking a "big jump" away from your current roles, routines, relationships, and assumptions and exploring new horizons.  This can also be thought of as "stressing the system" in your life or organization.  Most biological systems thrive when stressed periodically, so they adapt, improve, and shed unnecessary and inefficient uses of resources and energy. This can also be true for your personal life or organization.
    2. Questions:
      1. What are 3 new, exciting, and uncomfortable skills you can pursue learning in-depth and practicing?  Perhaps even a whole new role for your paid work or volunteering work.
      2. What are some best case/worst case scenarios you can explore when thinking about 1 big adventure to take on (you'll have to define that too!)?  You may find the worst case scenarios, when written down and realistically examined, really aren't as bad as once thought.
      3. What kinds of circumstances would have to take affect in your organization or life to feel a sense of urgency, importance, and energy to transition and improve?
  5. The Easy Glider
    1. This is the "go where the wind takes you" mindset and is somewhat of a conglomeration of the rest of the hats of a transition.  More characteristically, it embraces each day and moment as full of possibility and allows it to unfold a bit more organically than the others.  However, there is some flavor of doing the activities you enjoy, engaging in stimulating relationships, etc. vs. pure trial and error (Searcher) or seeking dramatically new experiences (Adventurer).  They are often open to anything but are deliberate and in control.
    2. Questions:
      1. What's going on in your life or organization that you enjoy about it?  Take notice and pursue new versions of these activities and roles as they come.
      2. How has this hat shown up in your life or organization and what are some ways you see it happening in the future?
      3. What are some ways you can embrace and celebrate right where you are in life or in your organization?

These 5 Thinking Hats are useful tools for your personal life, career, or organizational transitions.  I think many of us can identify with one or all of them, in our individual lives or perhaps as persona's of our organizations as well.  No mindset is necessarily better than the others and I believe they all have a useful perspective to at least explore in a thinking exercise.  I am certain deliberately stepping into a different mindset or "hat" in this case is a valuable way to explore an upcoming or existing transition, in our lives or businesses.  


15 Signs of The Reluctant Leader and What to Do About It


A Reluctant Leader is someone who has leadership qualities and has leadership roles but who may not be consistent, explicit, and continuously growing in these roles. My experience in Corporate America as well as in my work at Next Callings has brought me an appreciation for the characteristics and qualities of Leadership but also a keen eye for those folks (including myself!) that may be reluctant to take on acting as a leader or being known as one.  Problem is, when you look at some of the bi-products of these habits, is that being a Reluctant Leader could be costing you money, hard work, employee satisfaction, and ultimately your own fulfillment in the long run, whether its in your personal life or family, church, small business, or other organization. I believe Life & Business Transitions can be a lot smoother if one recognizes and improves on the qualities of Leadership.  I hope this post helps with that recognition and you take some steps to come out of your Reluctant Leader shell!

  1. You focus on the Why first and then on the What and How but don't necessarily communicate it that way.
    1. One thing to Do: Share it openly and often to reinforce, encourage, and improve.
  2. You know implicitly that there are Hard Things About Hard Things and make decisions that don't always satisfy everyone but you know that in the long run, most decisions you make satisfy most people, most of the time and are always focused on what's best for the organization and it's success for the long term.
    1. One thing to do: when you face a particularly Hard Decision, write out your thought process, how you've weighed the varying perspectives, pro's, and con's, then make the decision!  Reflect later in Retrospect not to judge but to learn on how you can make that hard decision a little easier next time.
  3. You genuinely do listen to others perspectives and opinions, whether they know it or not but you never end up letting them know!
    1. One thing to Do: provide constructive feedback, ensure the communicator(s) knows you're actively listening, follow up with reiterating/reframing of what's been communicated.
  4. You provide instruction, guidance, direction, and/or mentorship in service of your goal or vision for the business - it's not obvious that's what you're doing.
    1. One thing to Do: Keep it up but perhaps refine over time to deepen these relationships.  Ask how you can do better in this role.
  5. You work to bring people together rather than focusing on how to drive them apart - you're not sure why that is but do it anyway.
    1. One thing to Do:  This is a facet of Servant Leadership, reinforce that teamwork and group initiative gets the job done better than the sum of it's parts.  Take more leadership and employee development training to refine your skills.
  6. You focus on removing barriers, roadblocks, and hang-ups that are in the way of productive and satisfying work but you think this is more about the bottom line than at least as much about helping people.
    1. What to Do: write out what this does for the bottom line but also what it does for you personally, for your employees, and for your customers.  See how this holistic view can be improved on and used to make an even greater impact.
  7. You're genuinely concerned about stakeholder and particularly employee wellbeing but they don't know it!
    1. One thing to Do: celebrate this explicitly, build on it, encourage it from others in  your organization.  It's a great thing to model, follow up to ensure the organization and people within it are developing here as well.
  8. You think about how your organization could do it's work and fulfill it's purpose faster, better, and cheaper but you aren't teaching others the same mindset and habits.
    1. One thing to Do: Make this explicit in how you work yourself, learn other methods and cater them to your needs and culture, and work to train others in a continuous improvement mindset.
  9. You're mindset and actions are transformational and transitional but sometimes transactional - but you aren't clear in your style and it shows.
    1. One thing to Do: Learn about transformational and transitional leadership and understand how it differs from transactional.  The Former are about treating people as ends in themselves, the later is more about treating them as Means to Ends, whether it's employees, suppliers, partners, or even customers.
  10. When you say no, it's in service of your bigger goal and vision, and when you say yes, it's much more impactful, meaningful, and beneficial for the organization but you may not be saying no enough!
    1. One thing to Do: Think about WHY you say "no" and find commons reasons.  Use those as future litmus tests and decision aids.  It's great to be consistent and clear.  It'll help you do better in the future and as well as help the employees to know more about how the business runs and how you think about priorities.
  11. You are present and future progress focused rather than dwelling on the past but you may only be doing this in your head
    1. One thing to Do: Have conversations with your partners and/or employees the demonstrates these focuses.  Let them see this operate in your daily life and how it benefits you and your organization.
  12. You're a continuous learner and you apply the lessons to your organization on a regular basis - from others, from books and written resources, from associates and friends but you're not sure of the benefit nor do you inspire others to do the same
    1. One thing to Do: Think of it like this, there is almost no downside to continuous learning, only if you go into overload/overwhelm mode and end up not retaining nor using it.  This being said, the Return on Investment can be huge if you apply what you learn only a few times in your work or life.  As a business owner or for life in general, getting huge returns is always great!
  13. You seek constructive feedback but you're treating the useless feedback and valuable feedback the same
    1. One thing to Do: Identify the people that give the best feedback but not just the ones that reinforce your current world view.  Look for the ones that challenge your thinking and help you evolve.  Deepen those relationships and maybe step back from the others.
  14. When you speak, people listen but you're not speaking quite enough and your people want you to
    1. One thing to Do: start with more simple one on one conversations to deepen your insight and how you're perceived by others.  Widen this to bigger conversations and group working sessions. Ask for feedback on what people value most about what you have to say and how you benefit them in their work and lives.  Act on it!
  15. You innately practice and understand that organizations (and people!) evolve over time and transition through various stages but you aren't clear on the details, success strategies, and best practices to move through them successfully.
    1. One thing to Do: Learn more about organizational dynamics, transitions, as well as for peoples macro developmental transitions as well as common micro or shorter term transitions.  Apply this learning to the benefit of yourself, the organization, and employees.

Reluctant Leadership is not a destination but I believe a stage of transition in itself.  It is that uncertain ground many come upon when they open a business, take on a leadership role in an organization, or face a transition in their family in which they must step up and help others move through the transition experience in a healthy and successful way. I believe if one reflects on some of these tendencies and works diligently to overcome them, they will personally reap benefits while also benefiting through group and organization.  If you have some more suggestions for Reluctant Leaders or some of your own stories of coming out of your shell, share them in the comments below!