Challenging Conversations: A Toolkit to Give and Receive Feedback - Part 1/2

The harshest feedback I received

Almost a decade ago, I switched from being an Engineer to a Product Manager. I was part of a 3-member team with an engineer and a designer tasked with building an MVP for a new product launch. My manager was a Director of Product and wanted me to give a status update to the team. So he set up a 30-minute meeting with the Directors of Design and Engineering and a handful of other leads. He also added an agenda with a list of exact action items he wanted us to cover in that meeting (read: he micromanaged.) Like most other companies, setting an agenda in the invite wasn't the norm at that company, so I hadn't read it.

I was the newest in the team and had trouble working with the designer. The designer wanted to "think more," and I, the PM, wanted to "work backward from the meeting deadline." Before the meeting, I wasn't too happy with where the design was but decided not to ask my manager to postpone it.

So we got into the conference room, and I started the presentation by sharing the agenda of what I intended to cover. Then I asked the designer to walk through the MVP wireframes. The meeting wasn't going well, but I kept powering through it.

About halfway in, someone asked a question, and I started to answer it. My manager stopped me mid-sentence, and here's how that exchange went:

Manager: "So Vishal, did you see the agenda I set up for the meeting?"

Me: "No, I'm sorry I missed reading it."

Manager: "So we're halfway into the meeting. You haven't done anything I suggested and wasted everyone's time in this meeting. This meeting is over. I want you to work on things I want and meet again later."

My jaw dropped to the floor.

Being a new PM and getting berated before my peers and leaders hurt my ego and self-confidence. It also upset me that it would shatter my credibility as a PM necessary to lead others with influence without authority.

For the next couple of days, I was visibly distraught. The other leaders at the meeting came to me to provide support, and even my manager came and acknowledged that his behavior was rude (but he didn't apologize for it.)

My takeaways

Instead of having a challenging conversation with me in private, my manager censured me in public. Conversely, I also decided not to talk to him because I did not have the toolkit or vocabulary like this one. So instead of talking it out, I justified it by telling myself that my manager must be under extreme stress, he is relatively new to managing people, he must be having a bad day, etc., so I should overlook his behavior.

This company had a very competitive culture, and although we shouldn't expect any coddling at workplaces, and we're all fallible sometimes as human beings, the one hard lesson I learned immediately that day, and have tried to model every day since, was:

Praise publicly, criticize privately.

What are Challenging Conversations?

Challenging conversations are discussions between people where there is urgency, stakes are high, opinions vary, and emotions run strong. This setting can be personal or professional, and the tips described here can be used for both, but the urgency is usually higher at work, so that is the main focus here.

Such conversations arise in 3 situations, and it becomes more challenging in this order:

1. To/from someone at a lower level - such as a direct report,
2. To/from someone at your level - such as a peer,
3. To/from someone at a higher level - such as your manager or another cross-functional leader.

These conversations can cover three topics, ordered by increasing difficulty:

1. Technical - like the quality of work artifacts, data-driven insights, and analytical thinking.
2. Soft skills - like writing, communication, and presentation skills.
3. Interpersonal skills - like getting buy-in, holding others accountable, and building rapport to work better together.

Challenging conversations can happen in different combinations of these situations, such as discussing technical skills with a peer or working better together with a leader.

Why not avoid the conversation?

It's essential not to put the conversation off for a few reasons:

1. Conflicts can hold us back from doing our best work. Letting out hard feelings is a helpful way to get back to business. After that meeting, it was difficult for me to respect my manager as a thoughtful leader, which prevented me from bringing my whole self to work. And unfortunately, after a decade, that experience has still stuck with me as one of the emotional lows in my career.
2. Instead of becoming a victim of the situation or our feelings, trying to fix things proactively can empower us and help us mature emotionally, which is a big part of leadership. I could have learned how to speak truth to power and grow my emotional vocabulary a decade ago by figuring out how to have it, but unfortunately lost the opportunity then.
3. Having these conversations is a deed of sincerely caring for others instead of just being superficially pleasant. None of us are self-aware of all of our blindspots, and these can provide others with the opportunity to grow.
4. Learning the skill to have these conversations will help you not only become a better leader but also a better follower. As you appreciate the challenge of initiating them with others, you will also respect the difficulty others face when having them with you. That will help you receive feedback better, which is more challenging, and help you grow faster as a professional and a person.
5. Looking for ways to resolve differences instead of ignoring or stifling them will help build more trustful interpersonal relationships, improve psychological safety, make teams stronger by establishing an understanding among your team where feedback is viewed as a positive opportunity rather than a negative experience, and uplift the overall culture to one of learning and growth.

Diversity of opinions helps build stronger products. Proactively embracing diversity and conflict, and learning to collaborate and negotiate with others to influence them is the most critical skill that can help someone become successful.

How do some conversations become challenging?

A vital step in self-awareness is to realize that humans are judgmental, and we make numerous assumptions about a situation or person by climbing the Ladder of Inference.

When we disagree with someone or dislike something about them, we quickly make up stories that take us from the bottom to the top. For example, if Tom was late to a team meeting for an impending launch, his manager could conclude that he's not serious about his responsibilities in that project or the urgency of the moment, overlooking his overall work ethic, and could give him feedback to improve. But the actual issue could be that Tom's kid got sick that day.

All animals have been biologically wired like this for millions of years.

Under stress, our brains experience amygdala hijack where our neocortex, the newest logical thinking part of the human brain which separates us from the rest of the animal kingdom, gets shut down and overtaken by the amygdala, the more basal primordial reptilian part. That then releases stress hormones like cortisol which shuts down our reasoning, completely replaces thinking with reacting, and put us in a 5F (fight / flight / freeze / fawn / flop) mode

In my story, given the hierarchy of rank and power, my manager chose to fight with me publicly, and I chose to avoid conflict and fled.

Managing the basic instinct that we're wired for is hard. All this happens many times every day to each one of us (whenever we feel annoyed by someone or something.) So it's necessary to develop the awareness that before we let our emotions cloud our judgment, our assumptions and opinions are only internal stories that our mind concocts and should be validated with others before we act on them.

Next Time: Tips for having challenging conversations

In the following article, I will share a playbook with tips, emotional vocabulary, and examples for having these conversations.

Note: Ideas in this article are borrowed from Radical Candor, Crucial Conversations, Non-violent Communication, The Power of TED, and my own experiences.