My Best Tips for Talking to Senior Executives

My Best Tips for Talking to Senior Executives

Q: I have a lot of trouble communicating with my boss and other senior executives at work. I’ve tried so many different approaches and none of them have worked. At this point I’m pretty sure I’m over thinking everything. What’s your advice?

A: This is one of the most frequent questions I get asked from my career coaching clients and from people on my team. If you get nervous talking to executives or if you get flustered and feel like a hot mess every time you speak to your boss, the first thing to know is that you’re not alone. I have to admit that even now after almost 20 years in business, from time to time things can still get a bit weird when I talk to senior leaders without a good game plan in place.

Some executives make it harder than others. I’ve worked with leaders in the past that seemed to make a point of being hard to communicate with. Almost as though making me nervous and seeing me struggle was a game for them. Thankfully, a lot of this alpha dog management behavior is going away as companies in most industries are evolving and growing. As an executive myself, my entire management philosophy is to make the people on my team feel as comfortable as possible. In my experience people are at their best when they feel confident and comfortable so I don’t really see the point in making them nervous and inflicting any unnecessary stress by being difficult to communicate with. I have to admit though, I haven’t always been this way, and I think we have a ways to go before that philosophy is widespread. Until the day where every executive has adopted this type of approach, we’ll continue to struggle to find the right way to communicate effectively with them.

In my experience most employees fall into one of two profiles when it comes to communicating with senior leaders.

The Wet Noodle

Let me start by saying i have no idea why I’ve tried to use a pasta reference to illustrate this point. But let’s go with it. Anyhow … most people fall into the wet noodle camp when it comes to communicating with senior managers. They want to be demonstrably respectful of their boss or executive leader. They also worry about their ideas being wrong so they try not to take a firm stand on any particular point of view. They tend to talk around issues. They tend to meander and preface and provide context instead of making decisive points. They constantly hedge and defer to the executive for his or her opinion. I’ve even seen some people consistently append a disclaimer to every recommendation they make. Something like, “I think we consider stopping this program …. unless you don’t feel that’s the right thing to do …”

Even though I can understand what leads people to this approach, it inevitably backfires, and can really do damage to your personal brand if you’re not careful. You don’t want to be a wet noodle. Yes, you want to be deferential. No, you don’t want to shove ideas down your boss’s throat. But you have to be decisive and provide value. When all you do is talk around in circles to your boss and never make any strong point, you are pretty clearly communicating, whether you know it or not, that you have limited value to bring to the table. You should be trying to make your boss’s job easier – not just talk around in circles and have her do all the decision making for you. If you haven’t read, David Marquet’s book Turn that Ship Around, it provides some excellent examples of what the ideal superior – subordinate relationship should look like.

The Rigid Rigatoni

Fewer people fall into this camp, but its growing. I see it more frequently these days as millennials move into the workplace. Obviously this is the exact  opposite of the wet noodle. In an attempt to appear confident and competent, some people are way to aggressive in how they present ideas and information to senior executives. This stems from a need to feel respected and can often manifest after a number of years operating in wet noodle mode. We give ourselves a pep talk before meeting with an executive. We promise not to be a door mat this time. 9 times out of 10 this ends badly. We present an idea too passionately, we stop thinking creatively, we respond badly to constructive feedback or alternative perspectives. I even see some people, in an attempt to not be seen as a wet noodle, try to talk with the executive like they’re bffs. They try to take it to the friend zone when they weren’t invited. This one makes me cringe a bit because I see it quite a bit these days and its embarrassing frankly. Unless you are actually close friends with your boss or an executive at your company, don’t act like you’re long lost buds … brah.

The impact of being too rigid, too friendly or too aggressive when speaking with executives is that you come off as cocky, reckless and disrespectful. You really don’t want to be here. So if you’ve found yourself recently getting into heated arguments trying to defend your ideas to your boss, or you’ve caught yourself trying to fist bump senior executives at work – you’re a Rigid Rigatoni and you need to stop.

Here are my 3 best tips for communicating with a boss or senior executive. Its an approach that has always helped me strike the right balance between being respectful and being decisive.

1. Lead with the Headline

Many of us make the mistake of taking too long to make our major points. We provide too much context. We work our way up to making our point. We do this because we we’re scared that if we don’t, our ideas will get rejected or the executive will assume we haven’t considered all the variables. That’s flawed logic. The best way to communicate with an executive is to lead with the headline e.g. “My recommendation is that we cancel the program – its costing us too much money and its not showing enough growth potential”. This way you don’t force your boss to sit and listen to a bunch of context – you just get to the point first – then you provide context.

2. Share your Thought Process

Once you’ve made the big point, now you can offer to walk the executive through the process you used to come to that recommendation. This is how you demonstrate your objectivity and the quality of your thinking. For example after giving her the headline now you can say, “… and I’d be happy to walk you through my decision process and the other alternatives I considered.” This way you’re now engaging the executive in the conversation and giving her a window into how you think – into your value. I talk a lot more about the decision making process in my book.

3. Ask for Advice

Now that you’ve given your boss the headline and offered insight into your decision making framework, you need to ask for advice or input to make it better. Inevitably your boss or senior leader is going to want to add value – that’s their job. Its your job to take that advice and use it to make your work better. So instead of being a wet noodle and saying “… unless you don’t think its a good idea”, you might say something like, “I’d love to get your perspective and advice on how to make this even better.” This way you’ve been decisive, you’ve shown objectivity in your decision process and now you’re showing respect by asking for advice.

By presenting information to executives this way you effectively balance between the need to be respectful and the need to deliver value. Your tone is decisive but not rigid. You aren’t entrenched in a position but you’re confident in a decision making approach which led to a recommendation.

Hope this advice was helpful. Let me know in the comments section about your experiences (good and bad) with talking to senior execs.

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