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Hard Conversations with a Boss

on the left, the red cartoon image of a head with confused thinking and confused speech. on the right, the blue cartoon image of a head with clear thinking and clear speech. in the middle, a blue arrow to show transition from confusion on the left to clarity right.

The Overview

Hard conversations with superiors fall into one of two categories: (1) personal advocacy or (2) team improvement. First, it is helpful to distinguish which type you need to have; if you try to blend the two, you may confuse your messaging and reduce impact.

Personal advocacy conversations involve you asking to have your personal needs met. They are important for career and personal growth, and they have high potential for short-term change.

Team Improvement conversations involve you advocating to change team dynamics. Over the long term, they will grow your career more than personal advocacy and, in a healthy working environment, they should be occurring more frequently.

If you believe that your situation has elements of both conversations (e.g. I lack autonomy, which is slowing down the team's progress), try to frame the conversation as a team improvement conversation first, and have follow-on personal advocacy conversations if problems persist.

The Questions

Before beginning any conversation, there are five questions to answer that will help you clarify your thinking:

(1) What do I/we need that I/we don’t have?

(2) What facts/observations can I share?

(3) How am I interpreting these facts?

(4) What solution can I request?

(5) How do I fear I could be received?

The Template

There are some small differences, but the formula for both forms of conversation is the same:

(1) Invite conversation (2) Establish intent, (3) Transmit facts, (4) Interpret facts, (5) Dialogue to request.

Below are templates to help flow you through the conversation. In the following section, you’ll find detailed descriptions.

Personal Advocacy Template:

(1) Do you have a few minutes?

     (2) I don’t want to ____, and also, I do need ____.

     (3) I’ve observed ____,

     (4) and it makes me feel ____, (because I ____.)

     (5)  What is your view?… I ask that you  _____.

Team Improvement Template:

     (1) Do you have a few minutes?

     (2) I really value ___ for this team. I don't want to ___.

     (3) I’ve observed ____,

     (4) and I think it's holding back the team because ____.

     (5) What do you see?... I suggest that we  _____.

The Details

(1) Invite Conversation. Before starting, invite the person into the conversation.

Keep it simple: "do you have a few minutes?" or "can I raise something that's been on my mind?" to establish collaboration and buy-in.

(2) Establish Intent. Start on the right foot and set the context for the conversation.

It's powerful to begin by saying your fear out loud. “I don’t want to [cause problems], [lose your trust]”. Saying it helps you establish good intent and show self-awareness.

Then, the focus is naming what you do need and feel missing. Make it simple and concise so it is easily understood.

For Personal Advocacy conversations: "I do need [autonomy], [recognition], [to be honest]”. Much of the time, we don’t pause to ask what we really need. This lack of awareness decreases the persuasiveness of our communication.

For Team Improvement conversations: "I value [collaboration], [trust], [etc] as core to our success." Identify the shared purpose or value that you believe is "at risk" due to team dynamics. It's best if you can pick something you know is important to this colleague. If the conversation becomes unproductive, return to this shared value.

(3) Transmit Facts. Describe the event, behavior, or pattern that you observed.

Use objective facts, avoiding labels and interpretations. I want to tell you what I've seen."

The facts establish the "scope" of the conversation, and I urge you to keep the focus as narrow as practical. If you could only provide one fact, what would it be? Provide additional information only if it adds new insight (such as a pattern). Don't overwhelm them. 

(4) Interpret Facts. Your subjective interpretation of the facts.

This is an opportunity to speak from the heart.

For Personal Advocacy conversations:

Communicate your feelings (it's a step most of us prefer to skip). Communicated properly, feelings help others better understand your actions and perspective. To "properly" communicate feelings, take complete ownership of them: "I feel ___, because I ____". The words "you", "she", or "they" should not appear. When you execute this step, your colleague is more likely to remain open rather than defensive for the remainder of the talk.

For Team Improvement conversations:

Focus on team performance. Describe how the observations relayed in step 3 are interfering with the value presented in step 2. How is the team being held back?

(5) Dialogue to a Request. To get what you want, you need to ask for it clearly.

Many of our problems in life come from our inability to ask for what we want/need. We expect others to know what we want and resent them when they don’t. But others cannot read your mind. Come into the conversation with a request to resolve the perceived tension and meet you/your team's needs. This request can be small, but it must be clear. To ask for something that you’re 80% sure you want is a gift to both yourself and others; you don’t need to wait for 100% clarity, as you might be waiting forever.

Before sharing your request, invite your colleague into the dialogue. You've shared your facts and interpretations, now ask for theirs: "I'm curious what your view is." 

Listen closely and ask clarifying questions. Check in with yourself: does this new information change my pre-planned request? Only deviate from your plan based on new and compelling information.

If your request (or a “compromise” request) is agreed to, you have a strong basis for future accountability. If your agreement is not held, simply ask: “can you update me on X?”.

If your request is dismissed, dig into the logic behind the dismissal with curiosity and respect. What is the alternative decision being made, and why is it preferable? Making the trade-off explicit will help raise unconscious thinking and clarify the decision to both of you.

As much as growth in your career will depend on your ability to initiate conversations like this, your growth will also depend on how you respond when your requests are not met. In these moments: (1) take time to process, (2) consult trusted advisors, and (3) always have a follow-up within a week, two weeks maximum.

Some options always include:

(i) "Accept" the "rejection". Oftentimes, being on a team means putting "we" before "I". Make your "acceptance" explicit so your commitment is understood.

(ii) Propose a comprimise or a new path forward. Make sure the structure of this compromise is as clear to both of you as the original request. Compromises tend to get muddied and vague.

(iii) Re-affirm the request. This can be powerful and effective, yet is rarely done.

(iv) Present "consequences". This is not a threat or a punishment. It is a tangible, reasonable outcome that you are committed to following through on, as your request has not been met.

The End!

Influenced by the following books: Crucial Conversations, Non-Violent Communication, and Thank You For The Feedback.

A Personal Advocacy Example

(1) Can we talk about something that's been on my mind? (2) I know the company has been going through growing pains and I don’t want to come across as ungrateful, and also I do want to feel valued and recognized. (3) I haven’t received a merit-based raise since I started here years, and I’ve been comparing my salary to industry benchmarks. I'm well below most comparables I see, by about $20K on average. (4) This makes me feel demotivated, like I'm not reaching my full potential, and has made me wonder if I should look for a job elsewhere despite otherwise being committed to this team and our mission. (5) Do you have the same view on my comp relative to the market? [ANCHOR REQUEST: Will you think about options, and come back to me by our next 1-1 call with your perspective on the opportunity to increase my comp?]

A Team Improvement Example

(1) Do you have another 10 minutes to discuss a concern I have? (2) I know we both believe in the importance of respect to a healthy functioning team. (3) I've been on our weekly product review calls and there've been two arguments between our sales and product teams with yelling and personal insults. On our weekly sales calls, we spend a lot of time complaining about slow development work rather than talking about pipeline development. (4) I believe this conflict has become counterproductive and is distracting both teams from our shared purpose of building an amazing product that our customers love. (5) what do you think? [ANCHOR REQUEST: we should get the sales and product leadership on a call to discuss the root of the problem and collaborative solutions.]


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