How to work with (and impress) executives

This is the part of the blog post where I introduce the topic, explain why it matters and give you some context. But I don’t think I need to do that with this one.

You are reading this either because you want to get things done and need the support or input of a busy executive (which you have found frustrating in the past) or because you want to impress your executive boss to progress your own career. But it’s likely both of those things.

Or you might be a chronic people-pleaser, Pollyanna-type like me who likes to make people happy for the heck of it. But enough about me…let’s get back to you and the tips.

1.       Be respectful.

For me, this does not require being a ‘humble subordinate’ but rather balancing selflessness with self-respect. It involves approaching your executive with respect but also expecting respect in return.

From your end, this respect can start with a bit of consideration for their circumstances, which are likely different from your own. So, instead of getting frustrated, try to understand their situation.  

Executives are busy people. You are one of many who are trying to get their attention or asking them for something, whether it’s additional funding, their expertise or endorsement. They also have a personal life outside of work so only have a limited number of hours they can spend in the office meeting all of these different demands.

They are making many decisions throughout the day, mostly within short timeframes and often based on summarised information. They place a lot of trust and reliance on their direct reports.

And they generally don’t deal with the easy stuff. It’s the things that people don’t want to or don’t know how to deal with that are escalated to them. These are questions that often don’t have a clear right and wrong answer.

Executives are often making strategic calls that are full of uncertainty, but that will possibly impact many people across the organisation and, for executive public servants, many people in their community.

As you can see, it’s not an easy job. Yes, they are paid the big bucks, but they are also under a lot of pressure and scrutiny - the buck stops with them.

So, the next time you book a meeting with an executive, call or email them, please have all of this in mind. Not because you should be submissive in your communication or act like a hyper-efficient robot with no feelings, but because you should reference your knowledge about their situation when preparing your communication.

On the flipside, the executive’s situation is not an excuse for them to disrespect you. No one should be yelling at you or belittling you. This is a professional environment and it’s perfectly OK to expect to be treated like a professional.

My tips assume that you are dealing with executives who behave like decent human beings and not like spoiled brats. If not, you might need to take this up with HR.

I am also assuming that you are being professional and understand what disrespect isn’t.

For example, in a meeting with an executive, they may interrupt you because the information you are providing is irrelevant or because they want to clarify something you said earlier. Unless they are shouting at you, they are not disrespecting you – they are just trying to be efficient with their (and your) time. So, instead of being upset by this, take it as feedback and adjust the information you are providing.

I also think it’s important to include their executive assistant into the respect equation. First, it’s the decent thing to do. Second, by-passing the EA when requesting meetings with the executive or not responding to the EA’s requests until the executive follows up with you directly, is poor performance on your part. It’s also unkind to the EA and doesn’t allow them to do their job properly. So, consider the EA as a member of your mini communication team.

2.       Have a client service mindset.

In the past, when you’ve been someone’s customer or client, you likely appreciated the providers  that were clear, targeted their communication to your needs and were reliable in terms of the quality of their service or product and the timeliness of their delivery.

Your executive will likely be looking for similar things, so make it easy for them to work with you. Approach them as a client – you are there to solve their problems, not the other way around. Or, if you are the one approaching them for something, then help them to help you.

If you need their input on something to progress a task or a project, be very clear about why you are going to them and what you expect or need from the interaction. 

For example, do you need them to decide on something because they have the delegation (or formal authority) to do so? If yes, then this is an easy one, just say so or cite the reference document or policy. Be sure to support their decision-making process by providing them with sufficient and relevant information.

If it's something  more complex, give them a few options, presenting the pros and cons of each. Approach it like a mini options paper.

Even if you’re just seeking approval to order stationary for your team, be sure you've got the best deal, are ordering from an approved provider (if applicable) and that you’ve checked the team’s office supply requirements. Tackle each task like the true professional that you are.

Or maybe you want to tap into their technical expertise or knowledge of the market, industry or organisation to inform your work. In this case, make sure you've done your own research and checked easily accessible information, taken it as far as you can on your own before you speak with them. It’s better to use the meeting to test your thinking instead of starting from ground zero once you’re in their office – not cool.

If you are escalating a problematic issue, make sure you're not delegating too much upwards. Don't just make it their problem. Make sure you've done what you can to resolve it or thought of possible solutions before you go to them. This will properly align your request to the scope of their role and help you to avoid underdelivering in your own role.

If you need their support with something, you can check out a past blog post on influencing without direct authority.

Other ways to make working with you a pleasant experience is to deliver what you promised in a timely manner or at the very least to manage their expectations when you can’t. I have tons of productivity tips on my blog, if you’re interested. And if time management is an ongoing issue for you, check out my post from last year on tackling common drivers of poor time management.

Another very important thing to do is to see things through. If you’ve been tasked as an action officer for something, it’s your job to see it to completion. Don’t wait for your boss to follow up on it before you start the work.

Be proactive - chase who you need to chase to get the information, feedback or the micro-decisions needed along the way. Keep the executive informed of progress so they know you’re still working on it, if you are experiencing issues, how you are tackling them and whether you need their support in pushing someone along.

3.       Layer your communication.

Now, we all know that we should target our communication to our audience’s information needs. But you can’t always predict whether an executive just needs you to communicate the highlights or, while you are presenting those, whether they’ll request a deep dive into one particular issue. And, of course, you won’t know which one they will take a special interest in.

Or you may be requested to prepare a 20-minute presentation for an executive team meeting and then right when it’s your turn to present, due to unforeseen circumstances, you’re only given 5 minutes to present.  

The best way to prepare for such situations is to layer your communication. At the very least, you should have two layers: the key points and the details.

The key points should always include whether you are asking them to do something (such as to approve a recommendation or to give you feedback on a draft policy) or if this is for their information only. The key points should also include the key pieces of information they will need to make a decision or to say that they are relatively informed about the matter.

If you’re unsure about the extent of the key points, read what you’ve written or practice talking through your points and try to get this to under five minutes. If it’s not a  complex matter, try speaking for only two minutes. Believe me, you can say a lot in only a few minutes and this exercise will help you to practice being more concise and to-the-point.

In terms of the details, this doesn’t mean that you should prepare 50 pages of material or have a one-hour lecture ready. The details are there to help you expand on the key points to a level of detail that will help executives better understand the issue, but not necessarily master it. It’s important to remember that this should be more about what they need to know and less about you showcasing your awesome knowledge of the subject matter.

Again, try to read your presentation out or practice talking through it, to try and keep it to the time you have been allotted in the agenda. If you keep your presentation to around 5 to 10 minutes, this will leave time for their questions or discussion, before it’s time for them to move on to the next agenda item.

Imagine yourself presenting this at a board meeting where you are one of ten presenters on the day, the board members are possibly hungry and tired, they are getting notifications on their phones or being interrupted by executive assistants with urgent news, some are pulled in an out of the meeting to quickly deal with urgent matters.

It is not an ideal environment, I know, but this is exactly why you should do a few practice runs on your own before your actual presentation. It will help you test and improve the length and the structure of your presentation. Also, if you are bored with your own presentation after only 90 seconds, the chances are the board members will be, too.

Now, the tips above are more about presenting in person. If you’re writing to your executive, check out my tips from last year about how to write to your boss, whether it’s through a report or an email.

4.       Know your stuff…or know how to find the right answer.

No amount of pleasant small talk or ability to meet deadlines can compensate for poor technical knowledge. Delivering poor advice, no matter how timely or succinctly, is not helpful.

Of course, no one is perfect and people make mistakes. So, know that you won’t get everything right 100% of the time. Also, with complex issues, there won’t be a clear right and wrong answer.

However, you can mitigate this by doing your best to ‘know your stuff’.

One way to do this is to prioritise continuous learning. Carve out time each week for reading books or online resources on your chosen area of expertise. Consider pursuing further studies or taking a short course.

If you’re in the early stages of your career and don’t really have an expertise, choose one. Don’t worry about selecting something that you can do for the next 40 years because your expertise will likely evolve over time. Choose something that you are interested in and get good at it – try to be the go-to person for that thing as much as possible. Even if it’s not the most exciting subject matter, you can build on that over multiple decades and either niche down even further or get more strategic, as your career evolves.

Another way to improve the quality of your advice is to ‘show your work’. When you’re providing the executive with the advice, show what it is based on, who you’ve consulted with and so on. This will not only give them comfort but will also force you to do your research before you provide the advice.

Even if your advice is based on ‘professional judgement’ (a fancy way of saying that it’s based on a ‘gut feeling’), explain what past experiences have led you to this conclusion.

Good luck and thanks for taking the time to read the post.