Rogue Leadership: How Successful Leaders Think Outside the Box

Hosted by Chris Dyer, the CEO of PeopleG2 – TalentTalk Radio features engaging conversation with CEOs, thought leaders and HR executives.  TalentTalk connects professionals who care about talent-related issues and having the cultural mindset to embrace the needed diversity of the workplace.

Today’s guests are Kim Ades, President of Frame of Mind Coaching and Kelly Perdew, Managing Partner at Moonshots Capital. To hear the entire show, click here.

On the show today, a seasoned leadership coach gives tips on removing thinking traps and a serial entrepreneur and angel investor shares the tricks of the trade.

Kim Ades Kim Ades

Kim Ades serves as the President of Frame of Mind Coaching, a coaching company that has a team of coaches that caters to individuals who are interested in making a major leap in their business and personal lives.

While coaching people, Ades looks at their way of thinking and how it impacts the things they do and their outcomes. Over the years she has seen that business leaders lack a level of self-awareness and reflection. It is the biggest area of coaching they require. They’re often too busy focused on getting things done one after the other that they don’t have enough space and time to take a breath and ask themselves if they are even heading in the right direction. Often, the most important thing for leaders to do is to take a moment to assess where they are right now. Ades also feels that it’s getting more difficult for employees to take a little break because their responsibilities are increased and so are the distractions. There’s always an email to reply or a meeting to attend or a crisis to tackle which makes it difficult for them to carve out the time for self-reflection. “Organizations are often reflections of the leaders thinking. For instance, if the organization is under chaos, it means that the leader’s thought process is also under chaos. There’s a trickle-down effect that takes place from the leadership to the entire company. Thus, it is important that the leadership’s thinking is clear and precise,” explains Ades.

Getting the Right Frame of Mind

While coaching her clients, Ades advises them to keep a journal. This helps her understand their thinking patterns. She often notices leaders falling into thinking traps. In order to avoid getting caught in these traps, there are three top things that extraordinary leaders do.

First, they are very clear about where they are headed and they consciously veer themselves in that direction when they realize they’re drifting. These leaders don’t get sidetracked easily because they know their destination and the path they have to follow to get there.

Second, they challenge their beliefs. If they come across a problem, they ask themselves how their thinking is impacting the stress or tension in the situation and how can they make the roadblock turn into an opportunity. They’re constantly challenging their fundamental beliefs about any given encounter, situation or context.

Third, successful leaders leverage their resources. They don’t carry all the burden all on their shoulders and instead look for resources that they can use for help. Not only do they leverage experts in different fields and subject matter but also optimally use other resources such as technology, support systems and structural systems that are accessible to them.

Roadblocks for Leaders

Having worked with several leaders, Ades has seen leaders often struggle with roadblocks. She has summed up the most common ones in a white paper she wrote titled ‘The Seven Thinking Traps that Leaders Encounter.’ They are:

  1. Tunnel vision: Some leaders have a single-minded vision which becomes a little robotic and makes them lose sight of the bigger picture. They tend to block out all the opportunities that come their way.
  2. Isolation: A lot of leaders feel like they’re all alone and everything about the organization is on their shoulders. They believe that if something has to be done right, it has to be done by them.
  3. Image Management: Some leaders are very concerned about what other people think of them. They tend to point blame outwards and avoid taking full responsibility. They’re constantly in a state of worry and concern over the opinions of others.
  4. Poor Decision Making: Leaders often make decisions because they have to be efficient and so they’re not always working with people who are aligned with the values. In a rush to move forward and in the urgency of taking action, they end up making decisions that aren’t always in their best interest.
  5. Complacency: Leaders often get in a rut and stop thinking ahead and assume things are going well. They don’t strategically plan for things coming their way down the road.
  6. Shortsightedness: On a daily basis, leaders have to constantly fight fires and deal with crises. It is easy to come out feeling happy about managing to survive in those tough situations. However, while doing so, they forget to plan for the future and ignore the opportunities in front of them.
  7. Fear of Failure: Sometimes leaders tend to be so afraid of failing that they get paralyzed and don’t take any actions.

These are the internal challenges that leaders face and they often trickle down to the rest of the organization, according to Ades.

Tools to Overcome Thinking Traps

While coaching leaders, Ades and her team of coaches look at the client’s thinking patterns in a variety of settings. They don’t restrict it just to the work environment. They look at how these leaders deal with their families, how they are as parents, siblings or children, and so on. Ades then tries to identify the patterns that crossover in these different settings. She asks leaders to consciously notice their feelings and mood. This helps them understand the mechanics of “thought mastery.” “One of the parts is that if you’re feeling angry or negative or mad or frustrated, that’s an indicator that your thinking is doing you a disservice and is pointing you away from what you really want. That is the moment to catch yourself and think about where you’re going and what you want because at that moment whatever you’re thinking is almost the opposite of what you really want,” explains Ades. There are leaders who are often frustrated with their team for a variety of reasons. This frustration takes them away from what they’ve set out to build and instead creates an environment of tension and stress. Thus, via her coaching, Ades helps leaders pivot their focus back to their goals and make them realize that their frustration is creating a bigger divide between where they are and where they want to be. Thus, helping them close the gap.

What Are You Reading?

Kim Ades is currently reading “Fanatical Prospecting: The Ultimate Guide to Opening Sales Conversations and Filling the Pipeline by Leveraging Social Selling, Telephone, Email, Text, and Cold Calling” by Jeb Blount. In today’s world a lot of people denounce the idea of cold calling but in this book, the author makes case for his viewpoint that if you’re not prospecting then you’re missing out on the biggest opportunities that are out there and that it is the best way to grow a business.

How Can People Connect With You?

Connect with Kim via her website

Kelly Perdew Kelly Perdew

Kelly Perdew started his career in the US Army as the Military Intelligence Officer. After his term in the military, Perdew went to UCLA law and business school where he was bitten by the entrepreneurial bug. That led him to being the founder and/or senior team member of nine businesses, five of which were successfully sold and two are currently profitable. In the last ten years he’s also been an avid angel investor for early-stage tech companies which led him to starting his current company, Moonshot Capital.

Angel Investment 101

Initially when Perdew became an angel investor, his decision to invest was driven by the entrepreneur’s passion and idea. Now that he has an official angel investment firm, he has added some discipline to the process and his guidelines for investing have become stricter. He looks for disruptive ideas that can potentially reach a $1 billion evaluation. Another important criterion is that the product has to be live with some customers so that there is a product market fit. The business should also have monthly recurring revenues to show that the idea is working and that it’s solving a problem and that there is an opportunity to grow the business. Additionally, Perdew also likes it if they’ve raised half a million dollars which is typically beyond the friends and family round. It shows that somebody else also thinks it’s a great business to be in. Also, since he’s been in the field for a while now, he has an influential network. Thus, if Perdew and his partner are able to apply their network and be able to help instead of just investing money, that would influence their decision of investing. Perdew vets about a 100 companies a month, of which they do a deeper due diligence on two or three and eventually invest in one every 30-45 days. Other than these guidelines, Perdew emphasizes on passion, perseverance and planning among budding entrepreneurs while making investment decisions.

Adding Value to Startups

When Perdew takes on an advisory role in a company, his contribution is in three primary areas. Firstly, company building where he takes the company from a mere 4-5 people to a 30-40 and sometimes even 100 people. He helps entrepreneurs navigate through the potholes and barriers and move ahead. Secondly, Perdew also helps in raising capital. It is not an easy process for people who haven’t done it often. Having enough experience in raising money, Perdew is great at offering advice to the founding team. Finally, business development is an area that Perdew has found his expertise in and he helps companies in that area.

Passion Project

Perdew is passionate about the companies he invests in. One of the companies he invested in earlier this year is called CrossChx which provides healthcare identity solutions. The company is revolutionizing the age-old problem of filling out hundreds of forms while visiting hospitals and doctor’s clinics by matching and tracking identity in the healthcare system. It consolidates the medical history of patients into one digital file that all the providers have access to. The ultimate aim of the company is to increase longevity of people’s lives by ten years.

Influence of Military on Leadership Style

Perdew was the winner of the second season of the reality TV show The Apprentice. After winning the show, he was often asked how his background in the military has helped his career. These questions impacted him a lot and led him to write a book called “Take Command: 10 Leadership Principles I Learned in the Military and Put to Work for Donald Trump.” Perdew strongly believes that the leadership lessons he learned in the military are directly applicable to the business world. Other than passion, perseverance and planning, the military teaches integrity and the ability to be flexible, which are immensely important leadership qualities.

Employee Engagement

According to Perdew, today’s workforce is incredibly intelligent. One of the things he has seen in successful companies is the idea of loyalty. When companies usually talk about loyalty it is usually under the garb of telling someone to work over the weekend or cancelling their leave. “What you don’t hear or see much about in run-of-the-mill companies is the idea of 360 degrees of loyalty where employees cover for each other and even the company takes care of them and recognizes and appreciates their efforts,” explains Perdew. This is a way of giving the employee a vote of confidence that the company is there for them just as they’re there for the company. This creates an environment where people are comfortable doing things that they’d otherwise feel uncomfortable about.

What Are You Reading?

Kelly Perdew is currently reading The Checklist Manifesto: How to Get Things Rightby Atul Gawande. The book shows what the simple idea of a checklist reveals about the complexity of our lives and how we can deal with it.