5 Signs Youre Not Ready To Lead

Author

Molly Cain, Contributor

July 29, 2015

A few weeks ago, I sat on a panel with several other executive women representing a variety of industries: technology, health, the public sector and finance. We were there to speak to a room full of female managers from one Fortune 50 corporation. Everyone in attendance had been flown in for this event because they had at least one direct report, if not several. They carried a lot of value for the organization.

The topic for our panel? Leadership of course, but it was specifically geared to toward leaders who are currently rising up from the millennial generation. Of which there are many right now.  These people are the next batch of individuals to run businesses all over the nation and they’re in a critical development phase right now. (after all the editorial about this generation, the world has figured out they can’t get rid of them, so now it’s time to figure out how to build them up)  

At one point in the conversation, a question came up about choosing the right leadership opportunity — how do you know? Does it just eventually land in your lap as you work for the same company for years or do you actively pursue it elsewhere? And then once you’re approached with said opportunity, how do you know you’re truly ready to take the helm? 

I noted there’s never been a specific moment you decide you’re ready to lead. Though I do remember a pivotal day that I got completely depressed at the thought of existing at that same level much longer. I knew I wanted a bigger piece of the pie and a chance to make decisions for an organization — and I didn’t understand the many people my age around me who were completely fine (if not apathetic) about their job situations. I started to have less in common with them. The next I knew, I got what I asked for. Then I realized that if it’s truly a growth opportunity and a big step, you’ll suffer from a great deal of Imposter Syndrome  like I did. And that…is when you know you’re ready. When there’s enough at stake, enough human bodies for you to be responsible for, a large enough budget or just enough of a challenge, to make you a tiny bit worried about how you’re going to pull it off. 

From my experience and working with brilliant professionals who still serve as great examples to me and I greatly admire — true leaders take the unknown (even if it’s simply living in their own head), champion a team around them and just make it happen. And they walk out with as many, if not more, people following them to the next big project. 

Okay. So you’re willing to embrace the insecurity that comes with more responsibility and you feel good about it (or at least as good as you can feel). But what else can you consider as you look to make a leap? As I’ve grown in my management experience and watched my mentors operate over the years, I’ve been able to see a few key traits that seem to represent milestones of growth and maturity from a leadership perspective. 

Here are five signs you’re not ready to lead. 

You don’t own bad results. 

Back in the day, I worked for an incredibly powerful team under the management of a very experienced and wise former consultant-type. After years on the road sharing expertise with companies all over the world, he had decided to settle down and try his hand at “boring corporate life.” He had a different vibe and didn’t manage like a traditional corporate clone – and I loved it. 

He took a lot of pride in how efficiently our team of seven operated, from fewer and faster meetings to perfectly honing into the rewards we individually sought for good work. We hunted and ate everything we killed — we were powerful together. When we were “on,” life was grand and the entire company had eyes on us. 

Then there was that one time, several months into a large, daunting and professionally painful (read: rolling out a new software to a technology-impaired traditional organization) our boss noticed something was wrong. We were arriving late and missing deadlines. We were whining. We were infighting. Morale and passion were at an all-time low. 

Unlike any other boss I’ve ever had faced with this scenario, this guy responded with ownership on the issue. And by that I mean he rolled into a team meeting one day with books in his arms. He lovingly shoved Why Employees Don’t Do What You Want Them To Do into each of our hands. And after a group laugh at the title and the content within, we realized he was serious. 

“I need to apologize to each of you,” he said. “I’m not doing something right. And we’re going to read this as a group and figure out where I went wrong and how I can help get you back where you need to be. This is totally on me.” 

He assigned each of us a chapter to review in every staff meeting going forward for several weeks and as a group, we figured out what each of our “issues” were. Turned out different for all of us (poor guy), but it was one of the most productive exercises I have ever been through. Things changed drastically when they got transparent and when he actually rolled up his sleeves instead of throwing blame. After that exercise we even began self-diagnosing and coming to him for coaching when we noticed more signs in ourselves or our peers. To this day, I remember those chapters and the point he was making to all of us. He felt responsible for the morale and actively worked to find a solution. 

Because of that experience, I got my first genuine lesson in leadership. Take ownership. It’s true what they say, sh*t flows downhill. But blame on failure should go straight to the top. That is, if you’re doing it right. 

You already know everything. 

Recently I picked up the book, Think Like A Freak, by Steven Levitt and Stephen Dubner (authors of Freakanomics). I’ve voraciously chewed through this thing since getting my hands on it, because right from the get go, it disarms you. They force the learner in you to admit something before you can successfully proceed too far into their pages. That you don’t know everything. (dang it all) 

According to these guys, “Despite spending more time with themselves than with any other person, people often have surprisingly poor insight into their skills and abilities.” 

Over the past several weeks, I’ve watched several startups struggle with their teams. Enough to where I sat down and churned this LinkedIn column out last week to vent my frustration. It’s a typical thing, co-founder disagreements, but it’s fascinating to watch from a mentor side of things. When you watch a CEO behave in these arguments, it can be even more frustrating, as this is the person who believes they’re ready to take a business to the next level. And they’re clearly not. Just the mere fact they’re arguing about who stole an iPhone or spent company money on an Uber is a nice example there’s a larger issue. 

But the way some of them engage with their team is absolutely nutty (no offense). And the lack of personal self-awareness or desire to grow on a regular basis, makes it even moreso. When it’s an inexperienced leader, oftentimes they meet a difficult moment or a wall with a total give up. And by give up, I mean we’d actually hear words similar to, “Well I’m the boss and they’re not doing what I said so I guess that’s that.” It was like we were talking to four-year-olds. No mention of compromise, no taking ownership, just complete belief they what they know right now is what’s correct and anyone who disagrees with them is completely wrong. 

As I mention in my LinkedIn post, it’s really disappointing to watch managers or titled executives willing to kill the baby simply to make a point . From the outside, that’s when we know they’re not ready to be CEO. And even if they live to see another day, you know that’s not the last time they’ll meet with opposition, so it’s sad to know these startups will likely not make it, simply because the wrong person — the person who already knows everything they think they need to know — has been given the lead. 

You waste people’s time. 

A few weeks ago, I sat in the back of a cramped, standing-room-only conference room at the offices of Green Parks and Golf (GPG), a small investment company in Dallas that works closely with our accelerator and Health Wildcatters, our sister program. It was not a glamorous evening by any means. I’m talking boxed meals, free water, cookies and small talk. Everyone invited into the room was carefully selected prior to receiving the time and details…and they were there that night for one reason. To invest. 

Only 23 hours later I got an email from partner, Carl Soderstrom, “We just closed $850,000 for the company.” It read calm and somewhat like we-do-this-everyday but I could feel the excitement and satisfaction in another proven moment with his business model. The recipient of this good fortune? A small Swedish startup working to prevent at least 85% of hair loss that occurs when one undergoes chemotherapy. They even came bearing three local clients, cancer survivors, with testimony to its efficacy. 

But $850,000 in 23 hours? That’s about $37,000 per minute (and that’s all the math you’re gonna get from me today). 

Why was Soderstrom able to execute this experience so well and seemingly so efficient? Startups and brilliant business minds crave to know that secret. Beyond the very smartly-designed community GPG has built around itself and the fact it enjoys lots of room in a region yet to be saturated by investors of their size, this success can be attributed to the one rule its leader follows. He absolutely refuses to waste other people’s time. 

Soderstrom is one of those leaders who moves at lightning fast pace once he’s made a decision and communicates with his stakeholders the entire way— and that’s key. He does this because he understands (and respects) the time of everyone he’s in business with. 

Unlike many investors and managers I’ve met over the years, this person lives and breathes by the understanding that time is money. Conversely so, wasted time is wasted money. For everyone involved, not just himself. 

“The process of  choosing to invest does not have to be lengthy and difficult,” said Soderstrom. “I generally know in the first meeting if I like management and feel they can be successful. Due diligence must be done, but in early stage companies, it does not have to take forever.  There is just not that much there yet. The sooner we’re done, and the money is in the company, the sooner it is creating value”.

Are there leaders or peers in your organization that move so slowly you can’t get your own job done? Or does your organization suffer from too much of the M Word? Meeting (ugh). Corporate America loves meetings, but they don’t do it the Agile way. They do it in the “maybe we can stall so we don’t have to actually work on this,” way. 

I’m not suggesting that if someone asks you to help them brainstorm, start down a path, chase them for a decision or two or work late some evenings (or a lot of evenings if you work for me), they’re wasting your time. That’s not always the case. Brainstorming and drafting is crucial when you’re working on something new. No, I’m telling you that you need to make sure you’re working for and with people who respect not only the value, but the time you put in. And if you find yourself sitting in a 3-hour meeting talking about font type or a 5-hour meeting with a terrible person wishing you understood how important they were…then I encourage you to think about how quickly Soderstrom raised almost one million dollars for a small Swedish business by simply sticking to efficiency. 

Beware anyone who intentionally wastes your time or disrespects the cost of your attention – remain hyper-aware to people like this and you’ll always be better for it. 

You think you’re perfect. 

Introduce me to someone who publicly identifies as a perfectionist and I’ll show you a future leader who will stand in their own very perfect little way when it matters most. High standards are great (and necessary) when you’re a leader. But it becomes a problem when having high standards translates into lack of flexibility or “complete freak out” when faced with a forced detour. That helps no one. 

You know the saying about best laid plans? That was coined because nothing is ever perfect — sorry to rip that rug out from under you. Even if you’re satisfied with the results, there’s always a way you could have done it better. Or 400 more ways. If you, as a leader, don’t realize that and instead focus on your small vision of perfectionism, you’re potentially derailing your team, spending way too much time on the wrong things or don’t have the strategic mind to take it to the next level (and that’s ok, some people just don’t). Just as project managers build risk buffers into their plans, so should you expect something to go awry and help your team execute Plan B if necessary. Leaders who can stomach a problem with some semblance of grace and only a small voluminous reaction (you’re allowed to blow up a couple times if it’s big enough) fare far better than leaders who are frozen in paralysis and go off the rails their plan goes awry. 

Perfectionists just don’t have the flexibility in them to maneuver around big issues. But to be fair — I’ll hire a manageable someone who considers themselves a perfectionist. Because who doesn’t like to have a team member who tries that hard? I’ll just never work for one.

You hired a clone. 

If you’re in Corporate America, I’m willing to bet you’ve taken some sort of personality test at some point over the course of your career. In the past, I usually took them because my superiors always wondered what kind of Type A/B hybrid creature I was (I’ve always been hired by one of two kinds of people only – a visionary or an operational genius – the personality tests are perfect ways for them to know how to use me). Or to determine how a team could get over the hump or start gelling a bit faster. I don’t know about you, but for me, it’s always interesting to see where I land on a scale and where I can be most effective with the people I work with everyday. 

Anyways. Recently, I brought a Culture Index guru in to analyze my team. We’re in a stage of intense growth and it was the perfect time to see where we all fit in the big picture so we could set ourselves up for future success. When he walked in the room, he had us all pegged. It was fascinating to learn about ourselves — but what was most important (and you should remember this when you take a personality test), we were there to gain insight into how our personalities mesh so we could operate in the most effective way as a cohesive team. It can be exciting to hear all about yourself so you can validate your crazy later, but always make sure you keep your ears open on how you can best operate with those around you. 

He began to point around the room, noting our skills, weaknesses and quirks. But most importantly, he noted one particular thing between me and my boss and between me and the first team member I hired. When I hired her, I chose someone I now affectionately call my “unicorn.” She’s a woman with skills I’ve never in my life attempted to hone, a personality and heart I genuinely admire. She also carries with her a unique social world that she protects fiercely so she stays balanced all the time. I knew when I read her cover letter, she was a great fit with me. And she is. She is…I am confident…my total opposite. And better still, she never wants to be like me when she grows up. 

My CEO did the same thing. She didn’t hire someone exactly like her. Nay, she had the profile of Steve Jobs (not kidding) and I’m not that. Nor did my personal profile indicate it. Score, we’re on track. But the strange thing was a portion of my profile clearly indicated many of my actions were hell bent on trying to be like her. 

He told us point blank that we needed to stop. She needed to stop forcing or encouraging me to operate and solve problems the way she does and I needed to stop attempting it. The message? The minute we both stand in our own corners and rely on the skills we possess in complement to each other (as it so naturally happens we do), our organization will be unstoppable. 

For me, it’s difficult not to aspire to be in her shoes. I love her presence on stage, her brains, her ability to resolve difficult and controversial moments amongst startup founders with the snap of a finger. But I understand, I didn’t join her to become her. If a leader is hiring the right way, they’re hiring you because you’re a culture fit and also because you’re explicitly not them. Don’t take that gift away from them and try to be someone you’re not. Rely on what you do best and you’ll be unstoppable too. 

And if you’re the boss or eventually want to be, don’t hire anyone, ever, with the intent to conform or control that person. Always hire to your weaknesses so you can be made better. Find a unicorn and roll with it. That is, if you want your team to produce big results, because that just makes you look more awesome. Win win right there. 

Molly Cain is the Executive Director of Tech Wildcatters the nation’s #1 investment program for B2B startups. She’s a recovering corporate executive, co-founder of Viewmarket and a regular leadership contributor to Glass Heel and Forbes. When Molly’s not in the office, she’s doing yoga, hanging with her two rescue greyhounds and finding new ways to take advantage of her ADD. 

This article was written by Molly Cain from Forbes and was legally licensed through the NewsCred publisher network.


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