The Biggest Mistake Employees of All Levels Make – And How to Fix It

Achieving Goals, Confidence, Leadership Coaching, Mindset & Mindfulness
01/23/23 - Nicole Wood
team working together

In my career, I’ve managed everyone from very young professionals straight out of school to seasoned leaders with decades of experience. Despite the wide variety in experience and background, I continue to find that almost all employees struggle with the same thing: proactive upward communication.

This sounds buzz-wordy and like it’s just corporate jargon used to describe the way you navigate internal politics. That’s not what I mean at all. This isn’t a performative act to get your boss to think you’re great (though them thinking you’re great is a byproduct of doing this well!). 

What I mean is at any given time, does your boss know what you’re working on, how you’re progressing toward goals, what you need from them and what they can mentally archive?

In most cases, the answer is no. 

I’ve had countless conversations with other leaders struggling with this same thing with their team members. It seems almost universal that this is a skill that’s not only not taught but one that many are reluctant to develop.

Why is this so challenging?

It’s not natural to announce your activities like some kind of news reporter. You are focused on what you need to do, keeping yourself organized and getting your work done. It’s usually not top of mind to be sharing how meetings went, giving frequent status updates and occupying space in your brain to think about what someone else might need to know. It takes intention and time to build habits to do this well and not have it feel burdensome.

It can toe the line with micro-management. The pushback I have heard time and time again both when asking for this type of communication from employees and when coaching folks who are dealing with this friction with their boss is that it feels micro-managery. I completely understand that, and it can definitely get close to micro-management at times. However, I’d argue that providing extreme transparency and temporarily overcommunicating more than feels comfortable to you actually results in more passive management because your manager now knows what’s going on. They won’t feel they need to be so in the weeds. This is especially true if the relationship is new – trust is often earned, not just given.

What’s the result if behavior doesn’t change?

I have seen a number of work relationships devolve over time into messy arrangements where there is a lack of trust and frustration on both sides mainly due to poor upward communication. The boss is frustrated because they don’t know what the employee is doing with their time, and they jump to the conclusion that they aren’t doing enough. The employee is frustrated because they feel unappreciated and like their boss isn’t recognizing their efforts and their ability to do their job. No one wants this.

What’s the result when behavior does change?

When an employee begins to master this, there is a sigh of relief from everyone. The boss feels more at ease knowing what’s going on and not worrying that there will be an emergency a the 11th hour. There is increased trust and with that comes increased autonomy. The boss slowly disengages, freeing up time for both them and their employee. 

How to do it.

1. Give updates in real-time.

You may have spent a week prepping for a meeting with your boss. It went great. You’re buzzing coming out of the meeting and have your next steps ready to rock. Hooray! Your boss, however, is left wondering, “How did it go?” This is a perfect example of something that may not be natural or top of mind to you, but a quick Slack message or text would be perfect to say something like, “Meeting went great. I’ll update you more in our 1:1 tomorrow.” You don’t need perfectly packaged reports or well-written emails to give updates to your manager. Think about the simplest way you can communicate key information to them throughout the day or week. This regular flow of communication frees their brain space from wondering how you’re doing to focusing on what they need to be doing.

2. Provide visibility to plans and delays, not just results.

Very often I’ll hear from team members that they didn’t provide an update because there was no movement on a project or because the goal hadn’t been reached yet. No! This is when you should be communicating even more. This might be something as simple as saying, “My week got crazy busy with an influx of sales calls, but I wanted to let you know I haven’t forgotten about that project. I have two hours blocked off on Friday to work on it.”  

This also means escalating either for support or simply transparency when you encounter a roadblock. “I know we wanted the dashboards live by Monday. I realized a challenge with the way the system is set up, but I think I have a work around. Unfortunately this means that we will likely not go live until Wednesday.” 

Or perhaps your boss asked you to help with something that was a bit nebulous and requires some planning. Maybe the expectation is that it won’t be complete for a month, but that doesn’t mean that they don’t expect to hear about it for a month. A great starting point is a plan for how you plan to go about the project (this might be just a couple sentence email). Even better, you might assemble a task list or project plan that you share with them so they can follow along with your progress in real-time without you having to share an update and without them having to ask.

3. Really own your one-on-ones.

Your boss should not have to drive your one-on-ones. I repeat: your boss is not responsible for your one-on-ones. You are! I recommend having a shared location (a Google Doc, a project management tool, etc.) where you each can add agenda items in advance of your meetings. You should own:

A. Providing updates on key projects

B. Escalating things you need their support with or a decision on

C. Closing the loop on asks from previous meetings

I have so many one-on-ones that are wonderful conversations, but I walk away feeling unsure if we’ve covered the right things. What happened with that project from three weeks ago? Did we ever get paid on that invoice? How’s the team doing? In this article I talk about how to figure out what exactly should be on the agenda and how to determine what leadership needs to be updated on.

4. Put yourself in their shoes.

If you’re in the throes of this friction and feeling frustrated, take a moment to put yourself in your boss’s shoes. What pressures are they dealing with? Who is asking them for updates that they need to pull from you? What might they be wondering about? What is their communication and decision making style, and how can you best support them? Really thinking through your manager’s worries, goals and needs will help you preempt some of these communication challenges.

I know initially this sounds like extra work, but I promise you, if you follow these steps, you’ll see your career and your working relationships drastically shift in a positive way.

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