The Most Successful Leaders Do This Before Starting A Search for Their Next Job
Your future self will thank you when you make a more intentional decision about where you head next and why.
After months of indecision, Diana couldn’t take it anymore.
In 6 years, she had helped her company grow 3x, go public, and uplevel their operations. As a C-level exec of a mid-size, publicly traded, multinational company, Diana felt her responsibilities so deeply, it sometimes made her tear up.
She was loyal to her company's mission, the leadership team, and the thousands of people who worked across the organization she helped reshape and scale.
But no amount of loyalty could make her stay any longer.
Diana had been feeling the pull to look elsewhere for over 6 months, and yet it felt too scary to admit it.
Through major business and external challenges (i.e. the pandemic and major geopolitical upheaval), Diana was energized by her role. But more recently, she felt drained.
Her recommendations went unheeded and it was becoming increasingly difficult to represent the executive team’s decisions on various people matters that were detrimental to the performance and culture of the company.
As she contemplated her next role, Diana recognized that she didn’t want to take the first job she came across. She wanted to intentionally run toward a future role, not run away from her current job.
Diana asked me if I had a framework to help her reflect on her current role before she left.
She wanted to learn from her current experience to help shape the direction for her next adventure.
She wanted to feel closure: to celebrate the wins and make peace with the outcomes she was not able to realize.
Here are the 9 steps I recommended to help Diana digest her learnings from her current role and use them as inputs on where she should head next.
1. Your Wins: What Outcomes Did You Drive?
Gathering your wins is a great way to get started on your reflection as you likely have easy access to this information through your performance reviews and monthly and quarterly updates you prepare for your role.
How you do it:
List out the outcomes that you or your team drove in your latest role. These should be ones that had the most significant impact on:
The organization’s ability to maximize its impact or progress toward its mission
The team’s performance, culture, and wellbeing
The organization’s ability to deliver on its promise and commitments to customers and stakeholders
Gather details like the following:
Quantitative impact of the outcomes on the business and organization
Qualitative impact of the outcomes on the business and organization
Context for your goals and initiatives, including challenges and roadblocks
The role you played and key collaborators
For each of the outcomes you list, add 2-3 notes on what made the difference, including what you did well and the business context.
Example notes on what made the difference:
Delegated well
Strong strategic plan
Excellent, well-staffed team
Made necessary pivots midstream
Market trends created headwinds, but we addressed them
Additional reflection questions:
When did I go with my default behaviors and thinking? When did I choose an alternative path? Is there a learning to takeaway?
Were there particular objectives and goals that motivated me?
What made me more resilient and grounded in some of the more challenging situations?
When did I make particularly strong decisions? What drove me in that direction?
Why it matters:
These results will be helpful when you interview for your next role, and they are examples of how you put your strengths and competencies to work.
You should also think about which wins meant the most to you and why. The reasons will give you insight into your values, your interests, and where you might want to invest more of your energy in the future.
2. Your Misses: What Outcomes Did You Miss or Not Realize?
Less fun but just as important, you want to take stock of your missteps and missed outcomes.
How you do it:
List out the outcomes that you missed in your latest role. These should be ones that had the most significant impact (refer to the guidance I gave in the first step).
For each outcome you list, add a takeaway or two for your future learning.
Example takeaways include:
Setting more achievable goals
Making staffing decisions differently
Assessing and managing dependencies more rigorously
More effectively engaging in and managing conflict
Addressing capacity challenges more proactively
Changing collaboration approaches
Additional reflection questions:
Where were there goals that could have been set more effectively?
When did I make decisions that didn’t work out well? What made me lean in that direction?
Were there risks or opportunities I missed? Why?
What instincts did I have that didn’t serve me well?
You may need more time to reflect on these as they may trigger difficult emotions. You might feel disappointment, shame, blame, anger and a host of other challenging feelings. This is normal.
Your goal is not to create a long or a short list. Your goal is to create a list that honestly represents the highest impact misses.
Once you have your list and your takeaways, take the time you need to make peace with each of these.
They are in the past and cannot be changed.
You might be able to do something going forward and that can be a takeaway, but what you are seeking to do in this exercise is take stock, learn, and make peace with what you cannot change.
You can move forward and revisit this step throughout the process, but you won’t have completed the process until you can put the misses behind you.
Why it matters:
Understanding your misses helps you leave your current role without baggage and allows you to honestly assess why you missed and what you can do differently in the future.
You might have already completed these learning reflections in the past. If that’s the case, then take the opportunity to synthesize these learnings and identify patterns.
The patterns you identify can represent specific areas you prioritize developing going forward if you haven’t done so already. You can take a course, read up on the topic, or get a coach to strengthen your capabilities.
Your misses may also offer an opportunity for you to ensure that in your next role, you will hire and structure your team to complement you and support you in these areas.
Remember, your job as a leader isn’t to be perfect in all areas. Your job is to make sure that your organization, including you, has the talent it needs to be successful, which may mean augmenting each other at times.
Your misses will also give you a reference point for soft spots that may exist in your new organization. You can use these examples as reference points for questions you might ask in your interview process. You will learn more as a result and you’ll also convey your level of expertise and experience by the depth and nuance of your questions.
Lastly, being at peace with your misses means that you’ll be walking into your next role baggage-free. When we hold onto the misses, we are taking up space that could be used by more positive energy and creative ideas.
Giving yourself time to work through your emotions will mean much more room for success in the future.
3. Your Activities: What Energizes & Engages You?
Bill Burnett and Dave Evans in Designing Your Life offer a fantastic framework for determining how you should design your work around the activities that:
Energize you - When you do these, you feel like you have more energy during and afterward. You don’t feel depleted doing these activities.
Engage you - When you do these, you feel fully immersed and lose track of time. You easily find yourself in flow, you are not stressed, and your mind and heart are in the work.
How you do it:
The process for assessment is super simple.
As you go through your day, you note each activity and then provide a 1-5 rating (5 = highly energized or highly engaged) for energy and engagement.
After a week or a few weeks, you review the activities and look for patterns.
Why it matters:
You can take these insights to help you optimize your time even in your current job to emphasize those activities that energize and engage you the most and reduce your time spent on those activities that don’t.
Use these insights to shape your next role so that you are seeking and accepting a job that emphasizes the kind of responsibilities that are the most energizing and engaging for you.
4. Your People: Who Energizes & Engages You?
People are as important as the activities and the role you play. They can amp you up or bring you down. You will learn from them, be challenged by them, and grow alongside them.
How you do it:
You can repeat the assessment model that you did for Activities, but this time, simply list the people you engage with day-to-day:
Your manager and other senior stakeholders (e.g. the Board)
Peers
Direct reports
Customers
Partners
Vendors
List specific names and then give them each an energy and engagement rating of 1-5 (5 = highly energized or highly engaged). Notice any patterns in your ratings.
Does it have to do with their role in relation to yours?
Or perhaps it’s in the ways you collaborate?
Is there a particular context to how you work together?
How do you deal with conflict together?
Why it matters:
When you search for your next opportunity, the people will be among the biggest drivers of your satisfaction.
You want to understand what attributes will help you perform at your best. You also want to understand what behaviors might trigger your less than optimal responses.
You won’t be able to cherry pick all the people at your next job, but you can choose to avoid taking a job where your manager or closest collaborators possess traits that will be particularly triggering or difficult.
You can go into a role more aware of what works well and what doesn’t and create a plan for how to work with those individuals who are going to be more challenging for you.
5. Your Superpowers: What are Your Zones of Genius?
Your Zones of Genius are talents and skills where you stand out in your competency level and where you deeply enjoy the work and are often in flow when you do it.
These strengths may be capabilities you have known for a long time. It’ll also help to be open to the idea that these aren’t static and that they may have shifted.
You might still be excellent at something, but you no longer enjoy it anymore. That is OK, and it’s incredibly valuable to be aware of that change.
How you do it:
Take a moment to list out your top strengths. Don’t aim for a specific number. Just focus on what comes to mind first.
A strength is only a zone of genius if you are:
In flow = mark with an “F”
Enjoy it = mark with an “E”
Want to do more of it = mark with an “M”
Write down each of those criteria next to each strength. Only those that meet all three criteria (“FEM”) will you want to invest in seeking more of in your next role.
For each zone of genius, write down three things:
(1) How it impacts your outcomes, your business, and your team
(2) A brief example to help make this vivid
(3) Do you want to do more of this or less in the future
Why it matters:
Just because you have a strength doesn’t mean you want to emphasize it.
You can and should choose which of your strengths you want to prioritize going forward. If you aren’t intentional, it’ll be easy to take on a new role that has you leveraging strengths that don’t feel fulfilling.
Instead, use exercise to be more intentional and narrow down which strengths you want to focus on in your next role.
6. Your Kryptonite: What Frustrates You?
Often our kryptonite, situations and triggers that bring out the less-than-best of ourselves, are simply an overuse of our strengths. These are often areas of development or attributes where we need to find complementary talent to shore us up. First, we have to identify them.
How you do it:
Take a moment to list out your top areas of development or challenges. Don’t aim for a specific number. Just focus on what comes to mind first.
For each area, write next to it three things:
(1) How it impacts your outcomes, your business, and your team
(2) A brief example to help make this vivid
(3) Is this something you can tolerate in your next role or is it a non-starter
This list will now represent the range and severity of the frustrations that we want to avoid or what we might want to develop greater skills in navigating in the future.
Why it matters:
While we want to seek roles that bring out the best in us, finding a role that will have no challenges is unrealistic. There will always be some situations, people, and activities that may trigger us.
Once you have the list above, you will be better equipped to assess how a potential role and opportunity may lead you to exhibit some of your less productive behaviors.
You can invest in learning and development for yourself to lessen the negative impact of those triggers.
You will know better what questions to ask to learn more about a new role xt people surrounding it will provide you with an opportunity to have talent that will complement you and shore up the areas where you need support.
7. Your Values: What Matters to You
Most people struggle to clarify their values or start with ones that are vanilla and generic. One of the best ways to understand your own is to work in an organization and experience how a company (a) states their values and (b) lives or doesn’t live them. You quickly discover whether those values resonate with you and also whether living them or not living them matters to you.
This is one of those perfect moments where you can more easily reflect on which values you want to live out in your next organization.
How you do it:
List out the values of your current organization
Note for each of the values whether you found it resonated
List out additional values that matter to you (you can search online to find more)
Rank the values in the order that you think are most important to you in your next role
Next to your top 3-5, jot down at least one example of how you live that value and one reason why it matters to you
Why it matters:
Values are what underpin all of our day-to-day behaviors. They may be overt and openly discussed or they may be unspoken and implied. When you are clear about the values you are seeking, it’ll give you a guidepost from which to ask questions and explore with possible employers how their values and your values align or complement each other. The more closely aligned you are, the more likely it will be a good fit and vice versa.
8. Visualize: Embodying Your Future Role Meditation
Note: You can listen to this meditation in the recording of this post or as a separate meditation-only recording:
One of the most important ways to help you navigate this moment is to have a vision of your new role.
By taking a moment to feel the experience of the role that fully embodies what you are seeking, you will be better equipped to find a role that meets your priorities.
How to do it:
Find a comfortable and quiet place to sit. Ideally where you won’t be disturbed for 10-20 min.
Bring a notebook and something to write with.
Meditation:
Close your eyes and take a breath in and out.
Start to feel yourself supported by your seat and your spine to lengthen upwards.
Take another breath in and out.
Take a moment to relax the areas of your body where you might feel tension. Breath into those areas and if it feels comfortable, give them a gentle stretch or soothing touch or massage.
Breath in. And out.
Visualize your new role and how well-situated you feel in it.
You have a found a company where the leadership have values and exhibit behaviors that align with yours.
You are spending time on the activities that energize and engage you.
You are working alongside people who energize and engage you.
You are leveraging your strengths in your zones of genius.
You feel little or no frustration in your day-to-day.
You feel deep fulfillment and joy.
Pause this audio if you need more time.
Take another breath, in and out.
And when you are ready, open your eyes.
Take your notebook and jot down what came up for you in this meditation.
There are no wrong thoughts and nothing is too big or too small.
Try to avoid judging what came up and instead simply capture it. You will have time to review it later and make more sense of it.
After you have written down what came up in the meditation, set aside your notes and thoughts.
Give it a few days or even a week.
Then, consider either doing the meditation again or simply reflecting on your thoughts.
You might find that you have what you need to move forward. Or you might want to meditate again to see if anything has changed or shifted for you.
There isn’t a correct way to do this.
The meditation is meant to help you quiet your thinking about your transition and your next role and access your feelings and intuitive sense of these decisions.
Our thinking mind only processes one portion of what we observe. It also can be very slow on the uptake. Hence why you pull your hand away from something hot faster than you realize you might be being burned.
By accessing your other senses, you are leveraging more sources of intelligence. As a result, you will move forward with greater confidence and at times, with greater speed.
9. Summarize: What You Want (& Don’t Want)?
Congratulations!
You took the time to reflect on wins, misses, activities, people, strengths and frustrations, and you gave your thinking mind a rest while you tapped into your feeling and intuitive senses. Well done!
I recommend putting what you learned into one document or table of what you are seeking and prioritizing in your next role.
You can now use these inputs to help you start the search process knowing that you will be more intentional.
Thanks for the plan, but I don’t know if I can take these actions
OK, you’ve read all of the above, and you want to get started on them but are feeling unsure.
Some of actions might be incredibly easy for you to do while others you struggle with because they don’t feel clear or you feel uncomfortable with what is true for you.
To help you get going, create an overall timeline and set up weekly goals to move through these steps.
I also recommend finding an accountability partner who can help you stay on track and also bounce ideas off of to check your thinking.
Don’t overthink your approach — just get started and iterate as you go.
See this exercise as a time to invest in yourself and your fulfillment. Your future self will thank you!
I finished the reflection steps. Now what?
Navigating your transition and executing a successful search could each be a book and definitely separate newsletter posts. (Let me know if this would be helpful in an email reply “Yes! I want a post on …” or in the comments below.)
Just because I don’t want to leave you hanging, here are three broad next steps that mostly involve gathering a list of:
Industries and companies that are growing and are interesting to you
People in the roles, industries, or companies you are interested in exploring
Questions to ask to better understand if the role and organization will have the attributes that you are prioritizing (and seeking to avoid)
Your Turn
I’d love to hear whether you’ve done a reflection like this before starting job search or career change.
What has worked well for you?
What wasn’t worth the time?
Share your thoughts in the Comments below.
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This is fantastic advice Kathy. Many people spend more time planning a holiday to get away from a job they hate, than they do planning their next career move.
I've done similar exercises, and I've always found them enlightening and gained clarity. Then that clarity and having 'started' pushed me into taking the action needed to change my job.
Your process probes into what is important in a role and knowing that is the first step to getting what we want.