Bootstrap Leadership Blog

In all my years of coaching executives, I’ve come across some consistent development themes and behavior patterns.  Some of these challenges are easy to identify and craft development plans for, such as communications, developing talent, public speaking, conflict resolution, presentation skills, and listening more effectively.  All of these opportunities have one thing in common: there exists a fairly broad understanding of what these deficiencies look like, and how to improve them.  When my executive clients get this feedback, we roll up our sleeves and go to work.

Unfortunately, sometimes the opportunities are clear, but the feedback and the definition of the issues are vague.  In particular, there are four very common development themes that it seems no one does a good job of describing: strategic thinking, executive presence, learning the business, and judgment.  If my clients and I encounter these challenges, we know we have our work cut out for us.

I call these four the “Mt. Rushmore” of amorphous development opportunities.  Every time I hear a CEO say: “I think so and so could be more strategic” I always ask: “what exactly do you mean by that?”  It’s really important for me to pin down the CEO on specifics, so we know what to work on.  Likewise, many leaders get the feedback that they “lack executive presence” – which has many different variants, and has to be carefully probed (is it posture, clothing, gravitas, charisma?).   Sometimes, leaders are given feedback that they need to “learn the business” – but it’s never clear when they’ve “arrived” and learned it sufficiently, so that’s a tough one, too.  Finally, my clients and I really have to explore the depth of this feedback: “I’m not sure about their judgment.”  If we get this input, we have to really look for examples and dive into the nuances of what this might mean. 

None of these development challenges are insurmountable, but they all require careful examination to get the feedback providers (or manager) to be clear about what needs work.  If you leave it to others to define for themselves what presence or judgment looks like, you might make significant progress and still miss the mark of what they consider improvement. 

The lesson that I’ve learned is this – all development opportunities are not created equal in terms of simple and consensus definition.  Some of this feedback needs to be challenged, and carefully scrutinized.  The lesson that I hope you take away from this?  When giving feedback or offering an assessment, be very clear about what you mean, be prepared to share examples, and don’t rely on trite statements that can be hard to interpret or defend.  If you feel someone needs to “learn the business” better – bring specifics and your own clear definition of what this will look like.  It’s hard enough to find ways to improve in these four areas – the least we can do is help each other get a clear sense of how to improve.      

Let’s face it - you need your boss. Unless you work for yourself, the boss is still an organizational necessity, and a big part of your work experience. Your boss hands out work assignments, makes sure you get paid, keeps you from falling asleep in meetings, and hopefully protects you when you do something stupid. But sometimes the boss is the last to notice when you’re ready for something new. This is understandable. After all, they’re focused on making the team look good (not to mention themselves) and that can be a full-time job. No, it’s your job to manage your boss, and that includes telling her when you’re ready for something else. Like a new project or assignment, or even a new job somewhere else in the company.

Now, you have to bring a couple of things to this conversation. You can’t just walk in and say “I want to do something different”. First, you need to be on top of your current work – you better be knocking the ball out of the park, or asking for a better, cooler role is going to get you laughed out of her office. The one “must-have” for this discussion is a great performance record. It also helps to have a sense of the culture, and “how things work around here.” If you’ve only been in your role for a year, and the unwritten code is that managers need to “pay their dues”, well, you better factor that into your thinking. It’s probably going to be an issue.

Second, you have to bring a plan with you. You need to do your homework. You need to have an idea of what you want, and a few reasons why this is such a brilliant idea. You’re selling here, and you better be prepared to answer your boss’s questions. If you want to do more, why do you think you can take on more team members or responsibility? If you want to move to a new role, who will do your work? Who’s on the bench to replace you? Why do you need to make this move right now? What are your long-term career goals? Think through both sides of the conversation; anticipate what your boss is likely to say, feel and do – and be ready with your arguments. Prepare to defend your position, and try to steer the conversation toward why this is good for you and the company.

Lay out your ideal next job and the reasons why it makes sense. Maybe it’s expanding your current role or shedding some of what you do to focus on a specific task. Maybe it’s moving up in your current department, to a leadership position just above your current role. Or maybe it’s an entirely new job elsewhere in the company. Whatever it is, have your facts straight, and a strong rationale for your reasoning. Say: “here’s why I think this is good for me and the team/company.” Be firm, but don’t back her into a corner. The secret is to ask for her input and support in helping you achieve your goals. After telling her what you’d like to do, say: “I’d like to get your thoughts on this - what do you think?” And as the conversation goes along, don’t be afraid to ask for her support directly. Say: “can you help me make this happen?” or “is there anything else you need from me?”

Your immediate boss is probably the most important person in your work life, certainly as far as your career is concerned. Each boss you work for has the power to help you move forward, or put you in a box. They have the ability to accelerate your career, or frankly, derail it. Don’t be that manager who sits in the same job year after year waiting for the boss to offer a new and exciting role. Pull yourself up by your own bootstraps, and go out and make the case for yourself. If you don’t do it, who will? Do you really want to risk putting your career in someone else’s hands? Make your boss an offer, present it with passion and conviction, and appeal to her sense of pride in helping you move your career forward. If you’ve nailed your current role, chances are good that your boss will be there for you. Just don’t be afraid to have the conversation!

When it comes to leadership development, how big are you willing to dream?  How about a development journey so comprehensive that it will permanently change your leadership brand?  Welcome to the one-skill-a-year learning experience.  That’s right – a significant focus on one skill, for a whole year.  Let’s say the average leader starts managing people sometime in their late 20’s and has a normal 30 year career.  Even if you worked on just one skill a year, with this plan you’d master at least a dozen top leadership behaviors before your fortieth birthday, just when you’re hitting your stride as a leader.  Would you be interested in having world-class skills in that many facets of leadership?  Here’s how to do it… 

The first thing you need to do is choose the leadership area you’re going to work on.  I recommend picking a leadership behavior - actions you literally take on a daily basis.  For illustrative purposes, let’s pick “Driving Innovation” and plot a 12-month plan that has you moving through three integrated learning phases – study, practice and teach.    

In the first quarter of the year, you’re going to study – you’re going to hit the books, surf the internet, and tap into experts to learn everything you can about innovation.  Spend time in early January lining up your resources, buying three or four books on the subject, bookmarking websites, finding a conference to attend, identifying local companies known for innovation, etc.  Next, take all of your resources and planned trips and get them on the calendar; literally, carve out time every week from January to March to spend time with your favorite research topic.  Then, execute the plan.  By the time April rolls around, you’re going to know everything there is to know about innovation! 

Now it’s time for the next phase – practice.  Dedicate the next two quarters to applying what you’ve learned on the job.  Set up an innovation lab in your department or division.  Set a goal of brainstorming product or process innovations with your team.  Volunteer to lead a task force that is looking at new ways to innovate.  Write a white paper about the history of innovation in your company.  Make a pitch to senior leaders about the best opportunities for a new breakthrough.  In other words, roll up your sleeves and really get into it - make a concentrated effort to have innovation be a big part of your daily work life.   

Finally, in the last three months of the year, move into the teaching phase.  Volunteer to teach a course on innovation at the company university or organize and market a speaker series where you travel around the company giving talks about innovation.  If you don’t work in a large organization but like this development idea, look into teaching a course on innovation at a local community college.  What’s the point of this phase?  If you’ve ever taught a course, you already know – when you have to teach something, you really have to learn it. 

What do you think?  Can you do it?  A full year of development is ambitious, that’s for sure.  It will require a lot of dedication and perseverance.  But if you were able to do this with your three or four weakest leadership skills over a six to eight year period, just think how proficient you’d be – without question, you’d turn those opportunity areas into towering strengths.  Give this plan some thought the next time you find yourself frustrated about not improving a particular leadership skill or behavior.  Maybe all you need is the time and focus to do it right.