In Conversation: Timing Conversations, Delivering Bad News, and Being a Communication Chameleon

“In Conversation” is a series of interviews designed to extract tips on a wide range of topics from practitioners who do it every day.

An interview with:

Ithica Williams is a Project Manager and Growth Strategist at Clique Studios, and she’s also served as a member of our Inclusion committee. Prior to moving into the tech industry, Ithica graduated from Spelman College and then earned her law degree from Western Michigan University’s Cooley Law School, serving as an attorney for 5+ years.

Daniel Nelson is a Project Manager at Clique Studios, where he also maintains and manages our project management application software: Wrike. Daniel graduated from Carnegie Mellon with a B.A. in Chemistry and then worked as a healthcare consultant before joining our team.

Here, Williams and Nelson discuss how to best communicate with clients and coworkers.

When and How to Begin Unexpected Communication

In terms of timing your communications, are there any rules or recommendations that you use to help make it smoother?

Nelson: If you have the flexibility of when to schedule meetings, schedule the meeting based on your purpose. Understanding when to have meetings, as well as timezones and where people are in their own day, helps tremendously.

If you want to generate good ideas, you should start first thing in the morning. That’s when people are the freshest. If you want easy approval, you schedule right after lunch when people are tired and their bellies are full. If you want a quick meeting, you do it at the end of the day because they want to get out of there. Especially with sign offs, if you want a sign off, schedule it at 4:30pm.

Williams: Never give bad news at 5 o’clock on a Friday unless you have to. What would be the point of me delivering bad news at that time period and me ruining my weekend and a lot of other people’s weekends?

Nelson: Yes, with bad news, you’re going to mess up everyone’s weekend and you’re not giving people time to react within the work day. I would also go further and say: don’t give bad news right in the morning, because you’re probably going to mess up everyone’s day. But of course, sometimes you don’t have a choice.

How do you approach pulling someone into communication that they aren’t expecting?

Nelson: I use the Eisenhower Matrix: Is it urgent or not urgent? Is it important or not important?

When you’re not already engaging with people, your communication could be disruptive. So, I start by saying, “[Not Urgent, Important]” or “[Urgent & Important]” so they can know and decide for themselves when to address my question or concern. I’m giving information, and I’m giving it quickly so that way, I can leave you alone and let you focus on whatever work you’re doing. This is really helpful for remote work too when a lot of communication is happening over messages or email.

Williams: Yeah, you don’t want to interrupt someone’s flow if they’re trying to get something done.
When I’m reaching out to someone who isn’t expecting it, I first check their calendar or message the Project Manager who is in charge of their task at the moment to see if I can steal someone’s time.

I’m a person that likes to talk it out versus write it out so then, I’ll usually message and give a time frame like, “Hey do you have 15 minutes to talk through something on this project related to this issue?” That way they have a frame of reference of what I need and how long I need with them.

Approaching Tough Conversations and Communicating “Bad News”

As Project Managers, your biggest role is being the connecting thread between clients and our internal team. And oftentimes, you’re the ones who have to deliver ‘bad news.’ How do you approach tough conversations?

Williams: First, it shouldn’t be a surprise if something comes up. Based on previous conversations, a client should already have some idea that something could happen. So, I always start by acknowledging that we’ve talked about it before and then explain the situation.

I never just state the problem without a plan. I give a few options—with pros and cons on how each would impact the timeline or increase risks—and then make a recommendation for moving forward.

Would you say that having that open communication before something goes wrong is a key foundation?

Williams: Yeah. No one wants to be surprised. They want to be aware of risks and be able to plan for them ahead of time.

Nelson: Surprises are bad. If anyone is surprised about bad news, that’s a much bigger conversation. It’s better to give bad news early than to wait because it’s almost always going to get worse.

Another thing I do when I’m giving bad news is to shift from a blame mentality to a problem solving mentality. I don’t want to spend time fixating on the problem. That’s not useful. It’s more useful to shift immediately into fixing it.

A mindset that helps with this is using the collective “we,” as in myself, our internal team, and the client. I ask things like, “what do we think is the best way to figure this out?” so we approach it from a team perspective, not an individual perspective. It helps us stay focused on the future, not what led to the bad news.

You two are both using examples rooted in verbal communication, not written. Would you say that’s how you gravitate towards delivering bad news?

Williams: Yes, I never give bad news in an email. I send an email explaining the topic I want to talk about, so they can prepare beforehand and come in with some ideas, but then ask to schedule a call so we can talk through it, and I can answer any questions they have about it immediately. It helps avoid an email chain that’s back-and-forth and back-and-forth and any miscommunication that can happen in paragraphs of text.

Nelson: Same. And then I send an email afterwards summarizing the problem and the decision we landed on in how to move forward. It helps make sure we’re all on the same page again and also gives us a source to reference on the next call.

Building Rapport and Strong Relationships

You two are both really great at making connections with all different kinds of people. Do you have any strategies or perspectives that help you do that?

Williams: It’s easier to get to know someone when it’s one-on-one versus a group of people, especially if it’s a remote relationship and you’ve never met them in person before.

What I tend to do is mention something about them outside of work that we’ve talked about prior or even just something small like commenting on fall decorations or their style. Casual conversation helps crack that shell of a person, and you can have more of a relationship and fun dialogue with them.

Nelson: I will concept-drop all the time to hint at different interests I have. I’ll just try a bunch and see what they respond to. So, if I mention biking and they seem interested, I’ll know that’s a great way to connect with them to build that fast friend relationship.

Williams: Oh, I also compliment them.

Nelson: Yes! I love an Ithica compliment.

Williams: Building morale is so important. Communication is so much easier when people are positive and happy about the project. Even if it’s during a challenging or stressful time, I try to build excitement. No one wants to work on a project that has bad energy.

Do you change your communication style based on another person’s communication style? How do you approach making sure you’re meeting their needs and fostering the best conversation?

Williams: For me, I catch on pretty early on with those early conversations. And, if they’re more serious or straightforward, I get right to the point with them to respect their style.

Nelson: Yeah. I think it’s important to be sort of a communication chameleon with this role. I try to fit myself into whatever communication style they need.

For example, where do they fit on the “science to street” spectrum? If I find myself struggling to communicate, usually a switch on that spectrum helps us cut through to better understanding. So like, sometimes it works to say, “Yo. This sucks. I’m so sorry that this situation is garbage,” versus “We had a really unfortunate situation that arose.” Both are delivering the same message, but depending on comfort level and preference, a person could receive one better than another.

Other Resources on Communication

• Eisenhower Matrix | Eisenhower
• The Best (And Worst) Times To Do Things At Work | Washington Post
• 6 Ways to Build Rapport With Clients and Colleagues | Inc.
• 4 Communication Styles And How To Navigate Them In The Workplace | Atlassian Work Life