Maja + Terra Winston: Consulting & Leadership in Chicago

Maja Jovicic is a World Chicago 2018 professional exchange fellow. We are joyfully hosting Maja during her time in Chicago. We are amazed at everything she has done thus far. Being a part of the Holistic family, Maja has taken on the task of interviewing several fascinating individuals in our city.

Recently, Maja attended an event where she was able to interview Terra Winston. Terra Winston is a leadership consultant and executive coach, living and working in Chicago. She is the Principal of InTerract Consulting and ringleader of inTerractions, and has dedicated her life and career to unlocking the potential of every employee.

Terra Winston — Leadership Consultant + Executive Coach

Terra Winston — Leadership Consultant + Executive Coach


What inspired you to go into consulting?

What I realized when I was working in corporate, and also when I started my own business, is that the world is filled with amazing people with great stories and great skills. The reason why people don’t get to the levels they’re meant to be at, to the positions of power they deserve: it’s all little stuff. It’s politics, it’s skills that you don’t know how to use, it’s navigating this really murky world. Now, I don’t care if you’re in government, or if you’re in business for yourself as an entrepreneur or you’re working in any other organization of any type- trying to figure out how to play the game right stops a lot of really good people from getting to where they need to be.

How does your process look like, exactly?

First of all, individual coaching. Company or person hires me and we work on trying to figure out what are the blockers stopping them from getting to the next level. It may be that you are a really good worker, but you’re having some trouble managing people and motivating them. Some people are great technically but don’t know how to navigate situations politically. It’s one on one or me working with a smaller group, trying to identify the gaps and helping them find their own way to close those gaps. For larger groups, this shows up mostly as trainings.

Sometimes I do meeting facilitation. When you have a group of people trying to come to a decision – more than two people – coming to a decision can be a pain. You get a person like me to come in and design the conversation and help you get to the end points to move forward.

Lastly, I also do organizational consulting. Companies bring me in to take a look at their policies and practices, to put in programs to be more diverse, to help them create a better culture for people to want to be there, to be more engaged, and to help them put in place some programs that will make their managers and employees stronger.

Can you give an example of one of your projects?

I once worked with a company that was working on changing their business model, and in order to do that they needed to let go of half of their employees. They wanted to do it in the most compassionate way possible – I worked with the leadership team on this. It’s a difficult area, but it doesn’t mean you have to be terrible. We worked on the timing, the communication...

When it comes to organizations and letting people go, it is harrowing. The key is dignity- pay attention to when you’re firing somebody. Never ever do it on a Friday – you could have done it on Thursday, why make them come in an extra day? Never do it at the end of the day. Do it in the morning and let them leave. Do what you can do to connect them to a new opportunity – if the reason for the termination is organizational, you have a duty to these people.

You get to observe a lot of companies. What is your overall opinion of the way business is conducted in Chicago?

Almost every company has the intention of providing a comfortable environment. They mean well.

However, organizations are usually built around the founders and the people who provide money. What feels comfortable for them is taken as the company standard – but that doesn’t mean that everybody employed there feels the same way around everything. We built our processes around generalization, but when you bring in multiple cultures, little things matter.

For instance, we Americans love awards, but some cultures dislike being singled out because it’s embarrassing or dangerous. Those organizations that are serious about inclusion are trying to allow for some wiggle room, accepting that it might get messy and mistakes might be made, but the environment is what matters most.

Wiggle-room, messiness – aren’t these all indicators of some sort of friction?

Every time you break out of a norm, there’s friction. It doesn’t matter if it’s somebody from a different university, country, nationality, cultural or religious background, gender... inclusion matters because if I only talk to people with the same backgrounds and same experiences, we’ll be saying the same things. The world is running out of ideas – we need the friction of diversity to generate more!

Spend five minutes on google or whatever your search engine is. Search for millenials – there are so many articles, talking ad nauseam how millenials, by the nature of being born, are impacting cultures all over the world.

My favorite is an article that was very brutal about how “millennials are ruining divorce”. I remember reading this and going – well, that’s not such a bad thing to ruin! I’m pretty sure it’s terrifying to divorce lawyers, but guess what? It’s cultural change. Accept it.

Trends change and shift every day. It’s inevitable. This fear that new people are gonna change our culture – if you weren’t scared of it yesterday, you have no reason to be scared of it today. Adapt!

Check out our blog for more of Maja’s interviews.

To learn more about Maja and her journey with World Chicago, click here.