I dreamed last night that I pulled together the entire company for an impromptu meeting to discuss our company struggles and the immediate steps we need to take to turn things around.
Everything flowed perfectly, the right words, the right call to actions and the motivation was pure: winning.
In this dream I was working for a company that was struggling like no company had struggled before, at least not any companies that I’ve seen or heard of, and the entire management team sat confined in their rooms, towers of leadership, without communication to each other the challenge being faced by each and everyone of them: the company was not producing revenue and they didn’t know what to do.
In my role I was the VP of Sales, a role that I had worked in my career before within a couple of startups, but in this dream I felt stifled in a way that I have never felt in my life.
It was just as this dream was coming to its climax, or so I thought, that a key member of the management team sat with me after this blitz of an impromptu company meeting and asked me a simple question: what is wrong?
Three words: What. Is. Wrong.
It was in this point that the dam burst and I explained to him that I am going through the roughest period of my life and did not know what to do and felt incredibly stuck.
I felt so overwhelmed in both my professional life and personal life in this dream that I literally did not know how to move the dial forward at work and the cascading waterfall of stress in the office just seemed to paralyze me further at home too. As one of the leaders at this company I stayed within my leadership tower, hiding from the very simple question and the impact was a delay in my taking action, a delay in getting the others leaders to act, a delay in empowering the troops below to act and a delay in the opportunity to grow the company with sales being stagnant.
Human nature is full of pride and many leaders, at some point in their career, will undoubtedly deal with the challenge of this blog post: Admitting When You Struggle.
In my career I have taken many leadership positions, most recently working as an advisor the past 20 months for nearly a dozen startups taking on the leadership role to teach them, guide them, motivate them and help them grow their revenues by taking on the sales, marketing, product marketing, customer service and product management hats all within a condensed work period of eight hours per week.
Typically I worked in this advisory roles for an initial period of 90 days, to help give these startups both the right direction and kick in the rear-end to focus them, put in the right metrics, the right processes, hire the right people and point the compass in the right direction once they are ready to set sail on their own.
While not a single one of these startups I advised said the words, “I am struggling”, or “I need help” or “I don’t know what to do next”, they all did admit one thing: “We don’t know how to drive revenues.”
This is where I saw leadership come in, with each and every one of these startups, being able to show their desire to grow and saying they want my mentoring, advise and teaching on how to become a revenue-generating company.
If I were to wind the clock, go backwards in time to that initial conversation before they decided to bring me on as an advisor, I would have asked them the simple question: what is wrong with your startup?
I would have taken that question and then follow-up with questions that go a deeper into the psychology of the leadership team, helping them uncover where their obstacles exist and bring to the surface the most glaring challenges that maybe they have not yet been able to communicate before.
Any sales leader would tell you that they have faced both themselves, but also within their sales ranks, both above them and below them, the simple challenge of not being able to hit their company revenue targets, their team targets and their individual targets.
Sales quotas are put in place to drive the right behavior from each salesperson, managers are given sales quotas for their team and the heads of sales are given targets for the entire company. In many startups this cascade of goals are not in place, instead some pie in the sky numbers that were promised to investors or across the spectrum a very conservative internal target that was part of a general one-year, two-year or three-year plan but not broken down into team and individual components, nor metrics and dependencies documented as to how teams such as marketing communications, product marketing, product management, customer service and engineering can support the revenue goal.
When the startup starts pointing their compass towards revenue, they tend to have either lofty dreams or conservative goals, many times somewhere in between that range, but the vast majority won’t admit their struggles openly and therefore do not take the steps to do what it takes to make a change.
Leaders are always falling down, some are particularly good at hiding their scrapes and bruises. A hidden bruise, in this context, symbolizes the leadership’s lack of admitting to themselves and to their team that they are struggling with something.
I’ve seen this time and time again, from my first job delivering newspapers seven days a week as an eleven year-old for the San Jose Mercury News, scoping ice creams as a fifteen year-old for Baskin-Robbins, helping customers as an 18 year-old at The Home Depot, building a marketing team at NASA Ames as a 21 year-old, launching new products as a product manager at ActivIdentity as a 24 year-old, building a customer insight program at Mercury as a 26 year-old, taking on my first head of sales role at Arxan Technologies as a 28 year-old, closing enterprise deals at ClickTale as a 35 year-old to these past 20 months as a sales advisor to multiple startups including AppSee, Toonimo, UsabilityTools, xPlace and many others.
I’m now 38 years-old and through the evolution of my career, starting out in customer service and sales roles at retailers, through marketing communications and product managements roles at Silicon Valley high-tech companies, through sales roles at UK, Israeli, Polish and German startups the same challenge is faced: leaders fall down when they don’t admit their struggles.
The dream I had brought out that simple question, “What is wrong?”, which was such a basic question that none of the leadership team brought to the surface. The impromptu company meeting brought the light to the situation, with not a single person being able to cast a shadow on what everyone was being challenged with and as the company meeting progressed, and the positive inertia grew the possibilities to solve our revenue challenge were appearing almost like it was magic.
At one point I found myself walking down a row of people that seemed to be growing exponentially with supporters as I headed towards the back of the room. There was a troop of dancers, must have been eighty of them, all from California, building up a crescendo of buzz and then towards the back of the room was an NBA player, who I asked for some pointers on the outfits we would use as part of our tradeshow booth.
After the wave of excitement and rallying of the troops was over, everyone started heading out of the meeting and I headed back into the room to speak to my colleague who sat me down and asked me “What is wrong?”
It was after pouring out my struggles to him at work, the avalanche of stress I felt in not being able to find a solution and the impact it had on my personal life that I felt, finally, empowered and it was in that moment that I woke up from my dream.
Struggles are real.
Leaders fall down.
Leaders especially fall down when they don’t admit to each other and their troops that they are struggling.
I’d love to interact more with you on this topic, hear how you have struggled as a leader and if/how you overcame it. Engage me on my LinkedIn or Twitter, I look forward to engaging with you!