Taking Risks: The Elephant And The Rider

At one of my recent sessions in the gen-xyb™ High Tea program I run for corporations that are investing in the development and advancement of women leaders in their workplace, we had an opportunity to hear from some guest panelists about a topic that lies at the heart of the program: getting comfortable with taking more calculated risks professionally.

One of the panelists, a long-time partner in one of the big four consulting firms, and someone who has also been a friend to me for many years now and a cheerleader to me as I have taken my risks over the years, shared his thoughts with the group of women present. As powerful and impactful as they were, I felt it was important to share them with a broader audience so they could benefit so many other women out there that are taking risks of their own. At his request, I have kept his name out of this post, so have marked his responses as Anon. Enjoy reading, and I hope his words prove as valuable to all of you reading this as they have been to me and to the women in the room that heard them that day.

Daniella: How have you figured out what you need to know before taking a risk?

Anon: The way I make decisions in general, right, whether they be what advice to give to my clients or what advice I give to myself has evolved a lot. Frankly I’m at a stage now where I rely much more on intuition to make decisions. Now I don’t necessarily recommend intuitions for making decisions early in life. Through much of the first part of my career it was oriented around looking very analytically at situations. I just found for myself over time as I have accumulated more experience and got to know myself better and reflected on decisions I have made in my life I could see how intuition was becoming more and more important to me as a decision-making process and decision criteria.

So frankly what I tend to do is if it’s a financial situation I want to look hard at the numbers, I want to understand the numbers. I don’t trust per se other people’s analysis. But you do the number thing and then you step back and look more holistically at the situation. How do you feel about the situation? What do you think if in involves working with people? How do you feel about working with those people? If it involves products how do you feel about that company’s products and that company’s brand? Is this something you are going to have fun with and be proud to be associated with? Do you have a good feeling about it and do you think it’s going to work out or not?

I’ve recently interacted with a gentleman who has a decision-making framework and he talks about the elephant and the rider as the decision metaphor. The elephant is the unconscious and the rider is the conscious. His point is when a person is up on the elephant they are guiding the elephant but ultimately the elephant is going to do what the elephant wants to do. You have to recognize there is an elephant inside each of us which is the deeper contemplative part of ourselves and that is ultimately what is going to make the decision. We don’t want to be totally irrational and totally intuitive so we have to think about the analytical part of it but don’t be afraid to be in touch with deeper feelings about your situations and to go with it.

Daniella: How do I protect myself and my interests? How do you assess if you know enough to protect your interests, and if you are able to protect your interests in a situation?

Anon: I am quite a risk averse person. I come from a background where there is a sense of fragility around success…that’s my psychology. However, recognize that there is no way to avoid risk. The risk of not taking a risk is not taking risk. If you don’t take risk you’re not going to get a return. There is no silver bullet out there, really rewarding situations that don’t have risk associated with them. So if you don’t take risk, your risk is not having any upside.

By the way, most times risky things that you are contemplating are more interesting than the non-risky things. So the risk of not taking risk is having a dull life. So on the one hand I am careful about risk and I worry less about downside than I did twenty years ago because I have more ability personally to absorb risk. But you want to contemplate what’s a worst case scenario. If the worst case scenario occurs where does that place you, what would you do, what options would you have, how much would it hurt you?

There are times when you would say you know what, I would love to do this, it would be fun, I think there is upside, it would make my life more interesting, but I can’t deal with the worst case scenario. And that’s OK! Being able to ponder that decision is part of being mature and accepting we can’t always have everything we would like to have. On the other hand if you can contemplate the worst case scenario and you can figure out how you would survive that and pick yourself up and go on then I think you can consider whether you want to take that risk on or not. You can think about all those other things. Do I like the upside, do I like the people, do I think it would be fun? You can think about all those other things that might drive you to accept that risk in a situation.

Daniella: Have you at times given thought to whether you will succeed or not and related to that what other people will think of you? Do you even care what other people think of you?

Anon: Everybody cares about what other people think about them. If somebody says they don’t care what other people think they are kidding themselves and kidding you. But I also think about what I am going to think about myself. At the end of the day it’s about what do you think of the person you see in the mirror? If I feel good about the person I see in the mirror and if I project myself ahead and I believe I will feel good about that person if I go ahead and do this then I worry less about what other people will think about me if I do something. Part of it is being comfortable in your shoes and having an understanding of yourself. If you feel comfortable with where a decision may take a take you under a variety of decisions, including failure, then I would say go with it.

Daniella: Who have you found has been most helpful to you as you took risks and navigated through risks? Also where there ever people that let you down, and did you tell them that they let you down?

Anon: Generally I have benefited from very good mentors in my career. I was very lucky in that regard. Particularly coming out of a working class background and into a professional environment. Fortunately there were people generally in my career that were there for me and were willing to advise me when I needed it. I have benefited from great mentoring.

I think what is important for people to have as part of their lives now, particularly in big organizations, are advocates. A traditional definition of a mentor was an advisor. A more contemporary definition of a mentor is and advisor and an advocate. I would say in big organizations now in particular you need an advisor-advocate. Not just an advisor. Because you are competing with other people that have advisor-advocates. You need to arm yourself accordingly for that competition. I had great mentors.

Daniella: How do you know when to change plans or stop pursuing plans any further?

Anon: At any given time you look at almost anything and see scenarios for why it might still be viable. I think the decision process for when you stop is somewhat similar to the decision process for when you start. It’s a combination of the analytics and the intuition to make that call. But it’s tough. It’s particularly tough if your decision has consequences for others that may be part of that venture.

Daniella: How has your risk taking contributed to you developing your identity as a leader?

Anon: In my company part of my personal brand is as someone who is quite eclectic in the things I’ve done. I made a decision about ten years ago that I thought that traditional tracks in the organization were too crowded. But I love the firm, the people in the firm, and wanted to make my career in the firm. So I decided I wasn’t going to pursue traditional tracks – it was too crowded.

One of the metaphors I thought about is I’m not into yacht racing but I worked with someone once who is and there is this thing where if you get caught in the wrong spot, the boat that you are trying to overtake is actually using up all the wind that you need to overtake them. You can’t, you’ll never win by just pursuing them. You have to tack off and find some clean air and try to take another path. Even though as you look at it you say why would they do that, the finish line is over there, the other boat is over there, why would they go off that way? Because they have no chance of winning if they just follow the other boat. The air is dirty. The only chance they have of winning is to tack off somewhere else.

So I decided to tack off and do different things in my career. Going to India, it was phenomenal, what an amazing experience to spend time there and to get to know the culture and the people. Everything was starting fresh in a hot emerging economy. Doing things like that was part of me trying different things to create my own version of success if you will. I also have a much bigger external network than most of my colleagues in the firm because I focused less on inside stuff in the firm and more on the external world and built my value proposition based on my connectivity with the outside world versus my connectivity within the firm. That’s a little bit of a risky thing to do, because the safe path in a big firm is to create and leverage your connectivity within the firm. But I just felt it would be more interesting to me to create a value proposition based on external connectivity not internal connectivity.