Many clients come to me interested in some sort of change. Some experience a sense of burnout or languishing. Some are quite motivated and benefit from a thinking partner as they navigate their transition or reinvention. But there is a subset who itch for change and want to talk about that change but lack the tools or “task relevant maturity” to effectuate it. Some of those people are not ready for the big change but want to position themselves so they can be.
The problem this program seeks to fix is to help privacy pros, execs, lawyers, and teams develop the skills and mindsets they will need to effectuate the change they need or want.
Let’s talk about how we’ll identify your unique strengths, strengthen the areas where you need to get better, think big about the possibilities, and develop a clear plan to get there. Let’s find the version of yourself that can grow anywhere. Let’s create The Transformable You™.
Building the Strategy
Together, we will develop a strategy for transformation, but to do so we need a strategy for becoming transformable. The strategy is in three steps or “chunks”:
Step One – Discover the True You. We have to get clear about you and where you are now.
One of the guiding principles here is, “Don’t Kid Yourself!” It’s vital to be vulnerable enough to identify areas of development. History is full of people undone by their own hubris. Another important idea is being distinctive, finding what is unique about you. Seth Godin’s marketing book Purple Cow makes this point, that you must stand out.
To find the True You, we’ll use my Personal and Professional Self-Audit. We review six areas: a) strengths, b) skills, c) behaviors, d) subject matter expertise, e) networks, f) values. This work informs job searches as well as any other work the client wishes to do. It seeks to determine assets to reinforce, areas for development, and a picture of what is distinct or unique about you to differentiate in the job marketplace.
If you want, we can also do 360-review soliciting feedback from people you work with. But only if you opt in.
Step Two – Discover your True Direction. We get clear about your desired outcome or where you want to go.
This is not easy and may take some time. There’s a difference between wanting a change and knowing what it will be. You have to think about your finances, and about long-term hopes and dreams. We connect this thinking to the discovery work of the True You. Relevant questions here include (but are not limited to):
- What do you long for?
- What is the work you want to be doing every day?
- Will just a job change be enough?
- Like Lewis and Clark, we might be exploring an enormous possibility just to see what is out there, without a sense of what to do with it yet. Herminia Ibarra’s book, Working Identity, is pertinent in this respect.
- What is your larger purpose, your “Big Why”? Rutger Bregman’s Moral Ambition invites questions about how you can make things better.
Step Three – Find your True Path Forward. Define “how” Step One and Step Two are connected. The “how” is the strategy for change.
“We’re not going to talk about what we’re going to accomplish. We’re going to talk about how we’re going to do it.” – Nick Saban
Like most strategies or models, it must remain flexible. My clients are individuals, so this approach is not an inflexible cookie-cutter approach. We tailor the approach to you, where you are now, and where you want to go.
How do we become transformable? Mindsets and Skills
Mindsets
These are the mindset changes needed to become transformable in 2025-26 (noting that these may likely have to be updated):
The Fitzgerald: Embrace the F. Scott Fitzgerald idea expressed in his 1937 work, The Crack-Up: “Before I go on with this short history, let me make a general observation – the test of a first-rate intelligence is the ability to hold two opposed ideas in the mind at the same time, and still retain the ability to function.” A lot of people don’t recall the next sentence, which is important: “One should, for example, be able to see that things are hopeless and yet be determined to make them otherwise.”
Stability While Searching: Transitions and reinvention take a while. It may take time to sort out this strategic plan. In the meantime, take steps to keep the job you have and thrive in it. If you were shipwrecked, you’d figure out how to eat today and tomorrow, then develop a plan to get rescued. You must ensure you can meet your obligations.
Forward-Facing: Rather than relitigate or rehash the past, it’s essential to look forward. What changes do we make now, for the future? This is the difference between feedback and feed-forward. (Marshall Goldsmith).
“Be curious, not judgmental.” It might have been Walt Whitman who said this, but it definitely was Ted Lasso. This mindset embraces forgiveness, of self and others. It also helps with understanding of emerging technologies.
Be Like Ike: Dwight D. Eisenhower once explained that leadership is, “Persuasion, and conciliation, and education, and patience. It’s long, slow, tough work.” Knowing this reality, and planning for it, is vital. This pertains to leading others or leading yourself. Repetition will be essential, as will some compromise, and it will take a while.
Big Picture; Context: Look beyond the issues in front of you. Explore the context of others around you: boss, stakeholders, peers, subordinates. Know what the organization needs, what is happening in your industry and your world.
Less Pride, More Grace: Simply put, this means think less about you, more about others. In most cases when you screw up, it’s because you had more pride and less grace in that moment.
Open to Change: This means at least being alert to the necessity of change. It also means being open to exploring how.
“Don’t kid yourself”: Seek the truth, no matter what. Hubris is poison. You have blind spots. You need other people to help you see them.
No Comfort Zones: There are no comfort zones. There are only Growth and No-Growth zones. Staying where you are will be uncomfortable, too.
Techno-Optimism Depends on Human-Optimism: There won’t be technological solutions to your problems. To succeed you’ll have to embrace the human element. Connect, unify, collaborate.
Choose Growth: When in doubt, choose growth. Even if others around you are stuck, find the thing that helps you grow. As James Hollis asked, “Does this choice diminish me, or enlarge me?”
Know Your Important Thing: Stephen Covey wrote that “Courage is not the absence of fear but the awareness that something else is more important.” You can’t find courage if you don’t know your Important thing, your Big Why, your purpose.
Be a Jazz Musician: Jazz players know the tune, the structure. They follow the bandleader, then improvise. They can follow the lead sheet, the broad outlines of the tune, and then build upon it. This means they are open to change, and they LISTEN. They pay attention to what is going on around them.
Skills
These are some of the essential skills for becoming transformable. We would of course tailor the coaching to address the specific needs of each client. This list may grow, too.
Ask For Help. You can’t do it all yourself. You’ll have to ask for help and have the courage and vulnerability to do so.
Attention over Distraction. Our environment conspires to distract us, but we are not without agency. It’s vital to develop the skill of resisting doom-scrolling, finding focus, connecting to nature, connecting to our capacity to pay attention. Clear priorities reduce distraction (see below).
Only Connect. This line from Howard’s End is right. Or as Peter Drucker may have said, “Communication is what the listener does.” It’s all about connection. Communication skills are important but think bigger and think of them as Connection Skills. These include:
- Public speaking
- Facilitating meetings
- Effective elevator pitches and networking
- Storytelling
- Interviewing
- Selling/persuading
- Listening
Keep Calm and Carry On. It’s a poster, but it’s good advice. You have to be able to manage your anxiety. Taking action helps: “Ambition without action is anxiety.”
Reframe. Any situation can be reframed to find some opportunity. This is an essential skill, whether reframing in the face of major setbacks, or reframing in the face of resistance in a meeting.
Design for Workflow. One of the causes of burnout is the overwhelming volume and pace of incoming work. One remedy is designing orgs, teams, processes, etc. to absorb work, re-channel if needed, and recycle work for adaptive reuse.
Prioritization and Time Management. The Ike Box or Eisenhower Matrix is useful, particularly when applied at multiple levels. This is a key component of the Stakeholder Engagement Analysis (SEA Change) that helps with understanding of larger context. The “Weekly What Are We Doing” email is also a helpful tool.
Connecting the Dots. Being able to see how things relate, particularly in fresh and new ways, is essential to innovation. Connecting stakeholders and points of view is essential to collaboration.
Super-Facilitating. (See HBR Sept-Oct 2025.) It refers to the team member (leader or not) who can drive innovation, promote collaboration, and deepen connection. It is a bulwark against the “unconstructive deference” of not wanting to be seen as pushy that fosters inaction.
Structure Your Support. This is the flip side of super-facilitating. The rising tide lifts all boats; other people growing can better support you. Helping your subordinates and peers grow supports you and your work; you are not alone. On a larger scale, think of the Mister Rogers exercise of taking 60 seconds to reflect on all the people in your life who loved you to where you are right now.
Finding the Value Proposition. An essential skill for privacy leaders, but it pertains to most initiatives. It’s premised on the idea that you must first find what is valuable to your audience. This results from connection, from being curious and not judgmental.
Stakeholder Engagement Analysis (SEA Change). Knowing what is important to others is key to the value proposition, and to any connection or persuasion. The Ike Box analysis at different levels is germane here. Learn to explore:
- What does this person need or want?
- What pressures are on them? What does their boss need?
- What are they likely to do?
- What would I do if I were them?
- If I were my boss, how would I handle me?
- It’s not about me, so what would their analysis be if they did not think about me?
Create Effective Decision Mechanisms. Who decides, and when? With what criteria? Creating the path to the decision – whether for yourself or others – is essential for collaboration and forward motion.
The Courage to Act. Once you have decided, you must act. This likely requires courage, which requires a connection to the Important Thing that supersedes your anxiety or fear. Being able to find it is a learnable skill.
Maintenance. As privacy professionals do in mature programs, developing the processes, rituals, and structures to ensure ongoing commitment to change requires discipline, and is a vital skill.