Whether you're an inspiring leader or a dear friend, you can't push someone to make a major change, no matter how obvious to you or glaring their need may be, until they are good and ready.
Everyone has a unique, and non-linear route to personal and professional learning. It twists, ebbs, and flows over time. Since we're heads-down working away in our careers, it’s always maddeningly easier for others to see what we may need to change, than it is for us to see it ourselves.
Remember that when you see a key habit, talent, or vulnerability ripe for change in someone around you. Of course you want them to want to change immediately when you point it out. Yet tread carefully -- check and see if they are a) good and ready to hear it, and b) ready to do something about it.
Be kind yet candid about what you notice, and see how they respond. If they tell you it’s “confusing” or “needs more examples” or “not really my issue” and they are otherwise unable to process it, don’t imagine they'll never get it – it’s simply a “not yet,” or “not now.”
Then, let it go, because it requires your patience and willingness to tune in to them over time to know if not now, then when and how? Then when the time is right, and they are ready, it's magic.
This approach is preferable to what you may be tempted to do, which is try and force a change through sheer will, bluntness, or fear. In fact, at these times, a certain “helper’s denial” can kick in -- much energy can be wasted “advising” or “giving more feedback” or “telling” (or getting a coach like me in there) in order to push someone along, cleverly ignoring the signs that they simply aren’t ready, willing, or capable of making a change. While they may seem to be up for it, especially when they see how badly YOU want them to need it, they are inclined to go through the motions, either too polite, or frightened, to say "no thank you" or "I don't have time" or "I don't find this relevant."
Why can't we force them into readiness?
As a coach, I am referred to those who are ready / willing, and those who are not. Here's a little trade secret: if you have to push hard, to try and force someone into making a change, it won't work, or it won't last, unless they are otherwise ready and willing (in which case, forcing is overkill anyway.)
How do you assess when someone is "ready and willing" to change?
In short, when they say so. “I need to do something different.” Or, “I could use some advice or help with these new responsibilities.” Or, “I could use some coaching.” Or, “I’ve had a string of losses, and something needs to change here…”
Of course in addition to an actual request – from them -- you need to make sure they have the capacity and willingness to learn, and the timing is right for them.
Typically, we all go through growth spurts, followed by times of plateaux or consolidating our learning -- those cycles can be months or years long. It's good to expend your own energy, and/or make coaching or learning expenditures right before or during those periods of change or growth.
In order to do that, it's important to observe your people closely. Read them. How are they doing? What changes are they making? What are their pain points or issues that are apparent to them? Listen carefully for anything they might say about wanting to learn or develop professionally.
Short of that, maybe they express frustration about how they're doing their work, stuck in a pattern, coasting, or simply dissatisfied with their own way of doing things. At those times it's good for you to give very candid feedback about how they are doing or operating in their work, and what you see they could benefit from doing differently. Offer your support, and ask them how they'd like to work on that.
And when you are convinced they're ready, it's appropriate to give them support in the form of an empathetic ear, your candor, advice, and even professional training, coaching, mentoring, etc., as appropriate.
Another secret: have them focus on making small or simple changes in how they do their work that may have big impacts, rather than trying to change their stripes to spots. As an exec coach over the last 10 years, that's how I've come to look at the lasting changes I help my clients make.
How it works
The most disappointing development attempts in my career as a coach, and an executive before that, have been along the lines of trying to MAKE something happen when the person isn't willing and ready.
The most effective ones have been rooted in readiness and willingness to change. When your capable, willing person is ready for an upgrade in how they do their work, the outcomes can be significant -- and helping someone during those "good and ready"-to-learn times is among the most satisfying experiences.