Is your boss confusing & difficult?
3 ways to ask thoughtful questions at work
Welcome to the first official segment of the Future of Work on Substack! I’m so glad to have you along on this journey.
Here we’re holding healthy conversations about the future of work so that together, we can change the career landscape one leader at a time.
If you’re following along, I’d bet you probably have a story or two about work struggles, being a corporate misfit, navigating a winding path toward a never-quite-defined version of success, and striving to make a living while holding every ounce of happiness you’ve got.
A few years ago, I started to notice this general sentiment that everyone around me was just ‘making it to Friday.’ Because of my interest in this conversation and my awareness and intentional observation of people and their behaviors, I noticed (and you probably have too) that a lot of people are simply working out of necessity and accepting the status quo of whatever their reality looks like because, well… that’s just the way it is.
This narrative breaks my heart. Maybe that’s dramatic, but it’s true, nonetheless. I know that we all come from different backgrounds, carrying a slew of hurts and hang-ups (not to mention terrible work experiences). I know we see our work through our own personal lens that tells us one truth or another about the way things have to be.
But what if things - for you - didn’t have to be anything other than what you decide to create for yourself? If you’re just the slightest bit curious about exploring that question, you’re in the right place.
Let’s get to it, shall we?
Communication Strategies that Eliminate Confusion
There are few things more frustrating than a confusing boss.
This is NOT your fault. If you work for a leader and often find yourself scratching your head after conversations with them, wondering what exactly they were trying to say, don’t blame yourself. We’re so quick to question our own understanding and doubt our capability, BUT… it’s more than likely you’ve got a poor communicator as a boss, and if you’re confused, it’s likely others are too.
Here’s a quick story about a time I worked for a confusing leader:
Can you relate?
Let’s unpack a simple and effective communication strategy that you can implement today to eliminate confusion at work.
Pushing back on confusion: How to Ask Thoughtful Questions
If you’re confused, it’s important that YOU speak up. I know this is difficult. For some, we think asking questions conveys we aren’t equipped to do our job. For others, we feel like we’re the problem and just supposed to know everything at all times. And then there’s the age-old insecurity that puts us right back in middle school where we wonder deep-down inside, “is this a stupid question?” I’m here to tell you, it’s not.
Asking questions puts you in the driver’s seat, elevates your authority, and invites others to raise the bar on their own ability to communicate.
Here’s how to ask thoughtful questions that produce clarity:
1. Repeat back what you think you heard
Sometimes clarity requires a little digging. If you’ve interpreted something one way, but you’re unsure if it’s right, respond by repeating back what you think you heard and then asking, “is this correct?”
Poor communicators typically use a lot of fluff words or unnecessary language to sugar-coat the truth or under-emphasize the reality of what’s being said. In these cases, it can be really difficult to cut through the noise and get to the point. If you find yourself working for (or with) someone who struggles to speak clearly, this response tactic can help empower you to find clarity while also holding them accountable to refine the way they express themselves.
In some cases (and I’ve seen this happen), when we work with someone long enough, we can pick up on their communication patters and learn how to ask the right questions up front to avoid confusion altogether. And if they’re attentive, they’ll often pick up on what you need to know and level up their communication approach.
2. Ask for specifics
I’ve worked with a lot of people who speak in generalities. In fact, I find myself doing this often as well. I’ve found that most professionals fall into two categories: vision casting/broad thinking and execution oriented/tactical planners. In my experience, most of us fall into one of these categories naturally, even if we have to operate in the other category for our roles.
When you’re working with vision casters and broad thinkers, they often struggle to think through the tactical details necessary to execute on a plan because they’re thinking at 100k feet vs. 5k ft.
Don’t be afraid to ask for specifics when working with a leader or colleague who struggles to provide details. In fact, consider taking notes and writing down your questions as they talk. This will allow you to maintain an engaged ear as you listen and come back to your questions at the end. This also allows for them to process out-loud, giving you the full picture and context before diving into your questions.
Think through what you need to know to be prepared and set yourself up for success. This could be specifics related to:
timing
budget
tactics
personnel involvement
roles/responsibilities
Make sure to ask specific questions if you want specific answers.
Too many people walk away from a meeting frustrated because they don’t have clarity but have failed to ask the important questions. The answers are there, sometimes you just have to work a little harder to get at them.
3. Process then respond
If you’re like me, you need a solid amount of time to process information before formulating a well-thought-out response. I’ve learned in many instances not to respond immediately because I typically have a lot of fresh perspective after I’ve given it time to simmer in my brain for a bit.
When it comes to clear communication, it’s always a good idea to think through your needs and then follow up with a thoughtful response. This response should do two things: summarize your understanding and identify the gaps. When you identify the gaps, you’re going to want to call out specifics and list out the questions you need answered in order to fill those gaps.
The reason this approach is so successful is because it’s proactive, positive, and gives you ownership. Instead of sending a complaint email voicing your frustrations, or talking poorly about your boss behind their back about what a terrible communicator they are, this approach shows you take your responsibility seriously and have identified the areas you need clarified in order to succeed with the task at hand.
Learning how to communicate clearly and effectively is long game, but I promise, it’s so worth it. Even when it feels sticky, frustrating, and defeating at times, just remember: you can’t control how others will respond, but you can control how you respond. Learning healthy communication strategies will help you stand out among the ordinary and give you advantage that has the power to catapult your career.
Question to consider:
Who in my organization is difficult to communicate with and why?
In what ways am I currently fighting for clarity with this person?
What’s one way I can push back on confusion and fight for clarity at work?
An Invitation to Chat
If you’ve ever felt stuck in your career or needed help developing healthy communication strategies, my inbox is always open.
And if you’d like to chat, I’m here. I offer free clarity calls - which is a fancy way of saying let’s grab a quick 30 minutes so you can unpack your struggle and we can see if coaching is the right next step for you.
No pressure, no commitment, just you telling me what you’re dealing with so we can come up with a game plan together.
Click here if you need this in your life.
Until next time,
