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Leading with Ambition, Reality Checks, and the 3 Questions That Change Everything
An old boss of mine and I used to debate how to address clients who had extremely lofty goals. Sometimes our clients would present with dreams of playing in the NBA, becoming a DJ, or becoming a social media influencer. Whether or not these dreams were attainable, one thing was clear – these clients were nowhere near achieving these plans in their current state.
But what if they could reach these goals in the future? What were we to do then? As clinicians we faced a conundrum. Was it appropriate to provide these clients with a dose of reality and guide them towards a more realistic path, or was it important to respect the client’s right to self-determination and allow them the chance to believe that these dreams would be achievable if they worked for it?
As business owners, high achievers, coaches, mentors, and parents, we face similar challenges with those that we are working with (yes, children count here too). There seems to be a fine line between being supportive and being brutally honest – and how to toe that line gets increasingly complicated the closer you are to the people you’re supporting and the greater the distance is between their stated objectives and current behavior. It’s a powerless feeling for a leader. The people you lead always want more, want better, or would prefer change, but few are willing to do what it takes to get what they actually want – and even fewer know why it is they say they want what they want. Do we tell them the truth or do we let them figure it out on their own?
I recently sat down with a client whose line of work, like many of my clients, has slowly eroded purpose in his life while also managing to hold him captive to a six-figure salary that keeps him stuck. This challenge – the challenge of the golden handcuffs – is one that I personally have felt and one that many of my clients have experienced as well. This client, as with the aspirational dreamers from above, all present with a problem. I want my life to be at “x” but it’s currently at “y” – so how do I get to where I want to go? Worse yet, for those fortunate enough to have financial security, how does a person muster the courage to walk away from that?
The way I work to resolve this for clients is the same tack I took with my boss. Rather than feel the pressure to provide answers, shoot down dreams, or be overly honest – I take the pressure off and just ask them the following questions:
- What do you want?
- What are you willing to do to get what you want?
- How much are you willing to suffer to get what you say you want?
Bonus Question for Anyone Who Likes Psychology: Why do you think you want what you want?
Here’s how this applies to my clients, and here’s how you might apply these questions to your life or those that you work with:
What do you want?
Many times we already have what we say we want.
This past week alone, two of my clients said that they wanted “financial freedom”. When asked what that meant – both responded similarly – financial freedom would allow them to be able to comfortably do what they wanted to do. That then led us to discuss what they wanted to do – wherein we unlocked that to be able to do what they wanted to do, they actually didn’t need any more money than they currently had. In other words, financial freedom was their go-to line but they didn’t actually want financial freedom to do what they want, because they could already do that. It was something different – something bigger perhaps – something related to the idea of doing certain things at a certain level of status – a vision of themselves that had not yet been realized. All fair, but that would be a different “want”. If what they initially said was true, and financial freedom was the key to do what they wanted, they already could do that – they didn’t need to work more.
Of course, the answers here are fine, but the point of this first question is to prompt you to think more deeply, as we did in the cases above. Don’t be convinced that your first answer is the truth. There’s likely a deeper meaning behind what it is that you want.
What are you willing to do to get what you want?
As the Mexican Fisherman Parable goes, are you willing to sacrifice what you have for what you supposedly want, just to achieve an outcome that you may already have had if you hadn’t sacrificed it? This question is particularly useful in providing the dose of honesty that we may feel compelled to offer. Rather than point out how unlikely one’s goals are, just ask this question instead.
If you want to be a DJ – an NBA player – whatever it is – you have to be willing to do things that others don’t so you can become what you want to be. If you’re not willing to make these trade-offs – and I mean – really make these trade-offs – then you’re not going to become what you say want.
As in the case of the aspiring DJ, or aspirational NBA player, it will become clear that they are not willing to do these things. That does not mean they are a failure or that their dreams are stupid. It just means that practically speaking they aren’t willing to do what it takes. Furthermore, it provides an opportunity to return to question one, as oftentimes people’s wants are tied to perceived status gains, rather than a more resonant meaning.
How much are you willing to suffer to get what you say you want?
All trade-offs have some degree of pain. It can be psychological or physical and is often both, but you must be prepared to suffer if you want to become who you want to be. If you’re willing to suffer, and endure suffering, you’re then willing to overcome the barriers to achieve your objectives.
As was the case with the client with the golden handcuffs, his ideals were clear, and while he stated he was willing to lose his job to pursue a more meaningful life beyond just his career, he wasn’t too sure if he would be able to endure the psychological pain of going from financially stable to unstable. This then became the question of greatest significance to our work moving forward.
Of course, there are no right or wrong answers here, and the wants can change. The real strength of these questions comes in what they unlock in understanding one’s motivations and willingness. Too often we can get caught telling others what we think they should do, critiquing other’s dreams, trying to prevent others from suffering by providing our wisdom preemptively.
Rather than feel compelled to comment, I’d encourage you to consider asking these questions instead. Those that take your leadership seriously will thank you.
Thanks for reading as always and if this resonates with you, share it with a friend!
Time to win the week 🏆
See you next week :)
– J
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