Managing Upward: Common Mistakes & 5 Steps to Avoid Them (+ Scripts)

Managing Upward _ Red Cape Revolution

Managing upward can seem like managing through a minefield.

One misstep, and . . . BOOM!

But let’s face it.

If you’re a smart professional who wants to do good things for your company and your career, you’ve got to master the skill of managing upward–effectively communicating with and influencing your boss and other leaders in your organization.

But how?

managing upward-how do you do it

How do we not only get heard by our leaders, but also communicate our points of view in a way that move our work forward?

How do we speak professionally but truthfully so that our leaders and companies get the benefit of our expertise and experience?

If you know you need to manage upward more often, then you’re in the right place.

In this deep-dive, we’ll review the common mistakes–mistakes almost everyone makes (so no worries–you’re not alone).

Then, you’ll get the roadmap: my five steps to avoid mistakes when managing upward, complete with scripts.

Finally, I’ve included a bonus: my conversation starter outline  so you can begin to map out the next chat you need to have when you’re managing upward.

Ready to dive in? Let’s start strengthening your conversations with your leaders today.

Common Mistakes When You’re Managing Upward

None of us was born understanding the language of our corporate culture. But we can learn from other’s mistakes, and use that wisdom to make different decisions.

Here, I’ve collected the most common mistakes and assumptions I see even the smartest pros making when they’re managing upward, plus what to do instead.

Instead of . . .Do this instead . .
Looking only at our perspective, not the leader’sLearn the leader’s beliefs, goals, worries and hot buttons, and position everything through their eyes
Hedging what we really need to say Outline the conversation in advance, and practice
Not making a specific askReverse engineer the conversation--get clear on your desired outcome before you begin. (I've given you a process to do this, below.)
Overwhelming with detailThink “appetizer,” not “meal”—if they’re hungry for more, they’ll ask
Trusting email, Slack and text too muchStop the online swirl. Schedule time to be face-to-face or on the phone
Allowing ourselves to be intimidated by role or personalityStrengthen our own beliefs about our value and contributions to the company
Only communicating in meetings or when asked Intentionally build the relationship with the leader all year long (trust=truth/time)
Letting one negative experience stop us from trying againLeaders are human and have good days and bad ones. Professional, polite persistence on issues you care about is the only way to move forward.

Five Steps to Avoid Mistakes When Managing Upward (+ Suggested Scripts)

These five steps are simple, and create a roadmap for you to follow.

Fair warning, though–following these steps isn’t always easy.

But if the issue’s worth discussing, then it’s worth following these steps to make sure you’re getting heard.

  1. Schedule it
  2. Plan it
  3. Show up
  4. Shut up
  5. Follow up

Each step also includes scripts you can make your own, so you’ll be ready with the right words to put these steps into motion.

ready to manage upward

Step 1: Schedule it

The “do you have a minute?” conversation usually fails. When we catch leaders off guard, their defenses can go up.

To ensure focus, schedule your conversation.

Scheduling a conversation also creates a deadline for you, so you stay accountable to yourself to have the conversation you need to have.

It also gives the leader a signal that this isn’t just a normal, everyday conversation.

As you’re scheduling it, consider the experience of both you AND your leader. For example, think through:

  • The best time of day and day of week
  • What’s happening before/after
  • Environment/surroundings: should you stay in the office or go elsewhere?
  • Ideal amount of time you need & minimal amount of time you need
  • Other things unique to YOUR situation

Suggested scripts:

Hey—would you be open to [having lunch/coffee/sitting down with me] for [x] minutes in the next week or so? I’d like to get your input on [an idea/a decision/a concern] I need to address, and I’d value having a little focused time with you to talk. [Day of the week and time] or [Alternative day of the week and time] look good for me—what works best for you?

[If they express concern and want to talk about it immediately:]

I appreciate that, but I’d really rather you and I schedule a time to talk in more depth.  Again, [day of the week and time] or [Alternative day of the week and time] look good for me—what works best for you?

or

It’s important enough that I’d prefer we plan it on our calendars. That way I can make sure I’m prepared and we won’t be distracted. So, does Tuesday at noon work for you?

Step 2: Plan it

Most conversations with leaders fail because we’re not clear about what we want.

 

So, answer these questions yourself, first:

  • What’s the outcome you want? What’s the specific ask?
  • What’s the smallest possible ask that moves you forward? What’s the wildest one?
  • What’s the worst possible outcome? If that happens, how will you respond? How likely is it to happen?
  • What’s the thing you need to say that you’re afraid to say?
  • What’s the thing you’re afraid to hear? If you hear it, how will you respond?
  • What’s YOUR unique issue or hot button you need to plan for?

Now, think about these things about your leader:

  • What have you heard him/her say or do, over and over again?
  • What are his beliefs, and how do they influence his behaviors?
  • What keeps her up at night?
  • Where does she spend most of her time at work?
  • How does the issue you’re addressing impact her?
  • How does the issue you’re addressing line up with his beliefs, needs, goals?
  • How does taking the action you propose benefit her, short-term and long-term?

Now that you’re clear, use the Bonus Conversation Outline at the end of this post to help you plan and prepare.

 Step 3: Show Up

 Showing up isn’t just about being on time.

It’s about being fully prepared, present, and in a relaxed but attentive mindset.

Try these strategies to show up ready and at your best:

  • Arrive early and breathe.
  • Assume positive intent—we’re all doing the best we can with what we know now.
  • Prep and bring notes if you like (if you feel the need to explain them, say “This issue is pretty important to me, and I wanted to make sure to make good use of our time, so I jotted down some notes I didn’t want to forget to share.”)
  • Bring a drink with you. It gives you an excuse to sip and take a quiet second during the conversation if you need it.
  • Drop the corporate speak—speak from the heart.

Suggested scripts:

These script fragments may help you convey emotion and paint pictures. They’re not intended to be used all at once—choose the ones that resonate with you and your conversation, or use them for inspiration to insert more emotion and create clarity in your conversations.

  • We both get that this is a hard topic to talk about . . .
  • Honestly, I may not get this conversation right, but I felt I owed it to you to talk about it . . .
  • If the answers were easy, we probably wouldn’t be talking about it now, right? Since it’s not, I appreciate you diving in deeper with me . . .
  • I’m raising the red flag on this issue . . .
  • If [issue at hand] were a boat, I’d be calling the Coast Guard. . .
  • Let’s hit the pause button on X so we can focus on Y right now, okay?
  • In my role as X, I’d be irresponsible if I don’t speak up when the train is off the tracks . . .
  • From where I sit, if X doesn’t change, Y will happen. (Call out specific consequences that cause pain).

Step 4: Shut Up

Once you’ve landed your pitch, stop talking.

Silence is uncomfortable, but discomfort is where the growth is.

 

Try these techniques to help you quiet your mouth (as well as your brain):

  • Take a sip of water.
  • Breathe slowly through your nose.
  • Smile.
  • Press your lips together.
  • Count silently to ten. 

Step 5: Follow Up

It’s your conversation, and so it’s your responsibility to keep checking in and follow up.

Polite persistence goes a long way toward helping you get the outcome you want.

Ask yourself:

  • Have you completed any actions that came out of the initial conversation? If not, why not?
  • Do you need permission or just awareness?
  • What needs to be said again, or more clearly? What’s the picture you can paint?
  • What will happen if the conversation fails? What will you do then?

Suggested scripts:

I just wanted to follow up on the conversation we had on [DATE] about [TOPIC]. I’d like to take the next steps on the [idea/decision/concern] I shared. Do you have additional thoughts to share now, or should I schedule a few minutes for us to talk later in the week?

 As a reminder, this is important because [your reasons you shared in the initial conversation] and that hasn’t gone away. When can we decide on a resolution?

 What do you need from me to close the loop on [the issue we discussed] by [DATE]?

BONUS: Conversation Starter Outline

 As you plan your managing upward conversation, here’s an outline that pulls it all together.

Use it to plan what you’ll say so that you can be focused, brief and most of all, confident.

1. Appreciate & acknowledge

Hey [NAME]—I really appreciate you taking time to talk with me today. I know how much you have on your plate, and I’m grateful for your time and insights.

2. Reinforce common goals

As you know, I’ve been leading the charge to [deliver the result you create], and I’m really proud of the work we’re all doing together to meet X goal [specific, big goal the leader cares about, in his/her own words].

3. Preview the ask

To help us get to X, I’ve been digging deeper into issues of Y and Z. I see a red flag I need to raise with you, and ask for your help.

4. Give supporting detail (but not too much)

My specific concern is that during a time when we need to operate like [X], I see [Y] happening. [Add any specific but brief stories, such as “For example, during the XYZ client crunch, I knew from my experience that our team needed to do X, but we ended up doing Y, with Z results.]

5. Connect to consequences and repeat the ask

 My big concern is that if we don’t do [your suggestion], we’ll end up at Y, and it’s my observation that Y won’t get us closer to our goal of X.  I know that’s not what you want.

 So, I’m asking for . . .

6. Appreciate again and set the stage for next steps

 I’ll stop now and want to hear what questions or ideas come up for you. Also, I’m not asking you to decide today—I just wanted to get this on the table now so that we can begin moving it forward, and I appreciate your openness to listening to my concern. 

Final Thoughts As You Manage Upward

No matter what level they’re at, your leaders aren’t perfect.

In fact, just like you, they’re human.

im human-managing up

Thank goodness.

Being human means we often do things in flawed, emotion-and instinct-driven ways.

And don’t kid yourself–even the most logical seeming human acts based on emotion and instinct much of the time (and it’s essential to our success, too.)

When you take the initiative to get clear on what you want, plan your approach, and then have a human-to-human conversation with your leader, you’re significantly more likely to get what you want.

Managing upward isn’t a game; it’s another way to serve both your company and your career. We need you now, more than ever, so try these strategies and bring your superpowers to work.

Need more help?

No matter what’s happening in your life at work, a 30-minute chat with me can help you get unstuck and move forward, fast.

Just hit the button below, and pick a date and time that’s available. Answer a few short questions, and then I’ll call you at the time you picked. There’s nothing to prepare–just show up right where you are. If, after we talk, it sounds like one of my coaching programs or courses will help you going forward, I’ll share details after our call. There’s no pressure -my goal is to be helpful immediately.

Spots fill up fast, though, so schedule yours now and start getting the support you deserve.

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Are You Getting in the Way of Your Team? 3 Warning Signs for Leaders