Emails to a Young Entrepreneur: Asking for Help

Day 125 of Self Quarantine             Covid 19 Deaths in U.S.:  138,000

Asking for Help

Flip Comic created by David Robinson

  1. Restlessness: You realize that you need to change your life, either because it’s boring or because it’s painful.
  2. The search: The decision to change. The search begins through books, courses, meetings.
  3. Disappointment: Looking for the right path. You become aware of your teachers’ problems and faults. However many strands of philosophy or religion you follow, however many secret societies you join, there are always the same underlying problems: vanity and a desire for power.
  4. The teacher: The most dangerous moment. Teachers are merely people with experience. Each path is different and individual, but, at this point, it risks being sullied and becoming a collective path.
  5. The signs: You leave your teacher when the path reveals itself – through signs. Through those signs, God is teaching you what you need to know.

Coelho, Paulo, The Book of Manuals (Kindle Locations 369-370). Sant Jordi Asociados.

Bainbridge Island, Washington USA July 30, 2013

Dear Mikhail,

Thanks so much for your kind letter. While I am unable to answer your questions on which of your new product designs is better, I am able to see a new energy and thoughtfulness in your designs that weren’t there when we started our journey.

With your gift of studying with the design masters at the Institute of Design, you already have a good sense of what it takes to give and receive help. Sometimes that help was hard to take, yet you thrived in that environment. As a continuation of that process, you asked Patrick for help and he pointed you in my direction.

A year ago I attended a David Whyte “Poetry in the Woods” workshop. One of the exercises was to break into groups of four and share reflections on “the art of asking a beautiful question.” I quickly shared that my mentor, Russ Ackoff, was the master of asking great questions and how much I strive to ask better and better questions. My exercise partner stopped me cold with “David asked us to reflect on beautiful questions, not great questions.” I was stunned at how I had mis-heard such an important exercise. Then, I really was stumped when I couldn’t quickly come up with a beautiful question.

“Human beings cannot quite believe the depth, drama and even the disappearances involved in even the average human life. Each one of us grows almost against our will into a steadily unfolding story where the horizon gets broader and more mysterious, the understanding of loss and mortality more keen, the sense of time more fleeting and the understanding of our own mistakes and omissions more apparent. In the midst of this deepening we have to make a life that makes sense: there is no other life than the one that involves this constant beckoning, this invitation to the fiercer aspects of existence.”

“Through the insights of poetry, this weekend we will look at the fruitful discipline of first finding, then asking, ever keener and more beautiful questions; questions that do not produce easy answers but which help us to re-imagine ourselves, our world and our part in it, and most especially, questions which work to reshape our identities, helping us to become larger, more generous, more courageous; equal to the increasingly fierce invitations extended to us as we grow and mature.”

SOLACE: The Art of Asking the Beautiful Question – David Whyte

What are the beautiful questions that you are asking of yourself, your team members, your customers, and your mentors?

This exercise seems so easy and is such an enchanting one – what is your beautiful question? Yet, I struggle with what is the difference between a great question and a beautiful question. After a year of channeling my favorite mentors and asking dozens of my colleagues I still haven’t found a good example of a beautiful question. David Whyte is his wonderful way stays quiet about actual examples.  Recently, I came across A More Beautiful Question which has a complete architecture of beautiful questions.

There is something in the gestalt of the student teacher relationship that makes it easier to receive and give help. Yet, we seem to forget that lesson when we move into the professional world of masquerading experts. Most of my life is spent giving help to others and “paying it forward.” Yet, I still find it difficult to ask for help.

One of the more painful situations where I was unprepared and had to ask others for help occurred on an Outward Bound (OB) trip to the wild rivers and mountains of Maine.  These notes are from my journal “Experiential Learning – Management Development the Outward Bound Way.”

The campfire is started and it’s time for the evening ritual of experience sharing. I don’t even remember what the question was. I just don’t feel up to participating. I listen though. I’m observing. There is something missing. People seem strained a bit, the real selves aren’t coming through. I withdraw even farther. I don’t volunteer. Susan won’t let me get away with it. She looks over and says “Would you please share your valuable insights with us or are you too good for us?”

I spout something back. It’s acceptable and I pass. But I really want to stand up and shout “what’s happening here?” Where is the real human that I know lies within each of you? Why are we just going through the motions? But I don’t. Not enough time to get comfortable that I can let the confronting me out in this setting. So I hunker down behind Fortress Self.

As we finish the group sharing, Bob W. who is Susan’s boss and will be accompanying us on our hike up Mt. Katahdin tomorrow gives us a preview of what we are in for. He briefly describes some of the perils of climbing above tree line and what equipment and clothing we will need for the hike tomorrow. Now he tells me.  All the stuff he recommends that I brought but didn’t think I would need for the hike are now thirty miles away in Dennis’s car. This list gives me something to worry about. What if a storm strikes and I don’t have all my wool clothes to withstand it? I will be a burden to the group. A whole bunch of thoughts are creeping in that haven’t been part of the OB experience.

I’m beginning to understand. WHAT IF I BECOME A BURDEN TO THE GROUP? I’m starting to touch on something. It’s getting to the heart of me. What if I actually needed the group? I don’t like where these thoughts are going. I’ve always been on the other side. The group has needed me all my life. As father, as a manager at work, others have been dependent on me. I’ve been the foundation. Now it might be switched. I might be a burden. I don’t like it. Shut these thoughts down quickly. I jump up and head to bed. Better to think about them in more of a fetal position hunkered down in the sleeping bag.

Dan, Beth, and I are in the same tent tonight. Dan wants to talk, but I want to be left alone with my thoughts. Some feelings I haven’t much explored before. I think I’m getting a glimpse of how Jamie must feel now. She keeps talking about being a burden and so dependent on me. She expressed concern that she can’t just go out and get the kind of job that will allow her to keep the same standard of living. I haven’t been at all sensitive to those concerns. Here I am in a situation that is real easy to get out of, with a team that will be disbanded in two days, and the potential for being a burden preys on me.

What’s triggered all this? Something simple really. I’ve left my wool hat behind in the car. If a storm should catch us on the mountaintop, then it will be one of the most important pieces of equipment since most of our body heat is lost through our head. I don’t have mine. I’m either going to have to make the trip without one and hope there is no storm, or admit my lack of planning and ask someone who is not making the ascent if I can borrow their hat. I don’t like either of these choices.

Sleep comes slowly. I am all wound up. I toss and turn all night. The unconscious is real active this night.

I’m awake long before the o’dark thirty wakeup call.

I’m real quiet this morning. I’m still trying to find every excuse that I can or alternative that I can for a wool cap. Nothing is in my bag that can come even remotely close. Well, what are my options? The only person who is not going to be hiking today is Susan. Everyone else will need their wool caps. Damn. She is the last person that I want to ask right now. I start rationalizing that not all of us would be stuck up on top of the mountain, so the odds are really with me. As usual I procrastinate and delay the decision as long as possible.

Well we were off. I had to make the decision now. Swallowing my pride I asked Susan if I could borrow her wool cap. I lamely explained how I’d left my stuff back at the car because the weather was so nice. She was very reluctant as the cap was very special. It was given to her by one of her sons, Nicholas, and obviously she had quite an attachment to it. It helped remind her of him when she was away from home on the OB trips.  Now I really felt crappy. I was about to walk off, and then she said “Sure. Take it, but please take care of it.”

I quickly tucked the cap away in my jacket pocket out of harm’s way, and started up the mountain. I had made the right decision and wouldn’t be a burden, but boy it hurt. I can’t imagine how it must feel to think of yourself as a burden to someone else day in and day out. It’s so subtle and acts over such a long period of time, that you don’t notice how draining it is. But worse, those of us who are apparently shouldering the burden are so incredibly insensitive. Which one of us in the end is more burdened?

While Susan has accompanied us up the trail this far, it is now time for her to go back down. She has a trick knee which does not hold up well when hiking. She is clearly disappointed and a little teary eyed. I wonder why and then realize that she’s had to face a much more serious version of what I was doing this morning. She doesn’t want to become a burden either. Her knee could give out at any time and then we would all struggle for the rest of the day trying to get her down off of the mountain. As a result she had to ask her boss, Bob W, to take part of his weekend to help her with her responsibility. She will now have to sit and wait while her charges are scattered all over Baxter State Park.

I can see my attitude towards Susan changing, but not enough to say anything right now.

Dana Dyksterhuis describes her hard work in remembering to ask for help:

“In the process of starting a venture, there is a lot.  It’s brutal. So you give up your life. There are a lot of sleepless nights.  I used to sleep like a baby, but not anymore. You are building something from the ground up and it’s not easy.

“When I spoke with the Women 2.0 group in Seattle, they had five pieces of advice for entrepreneurs and one of them was “Keep Going”.  Especially in our case you want to give up, you get nervous. If I hadn’t met Paul that night, I wouldn’t be standing here and Fanzo wouldn’t exist. If I hadn’t given that 15 second pitch and made a jerk out of myself, I wouldn’t be here.  Just do it.  Just totally go for it no matter how nervous and scared you are.

“The second one was ‘Ask for help.’ I got this from a software development bootcamp that the McCarthys put on at UW Bothell. One of their core protocols is ‘Ask for Help’ – the act that catalyzes connection and shared vision.’ What they taught us was that no matter what you are stuck on – ask for help. It sounds so easy, but it is incredibly difficult. We all think that we can do it. We can do everything. We got this. No problem.

“If you ask for help, you can get results faster.

“A specific example of asking for help occurred early on.  Sometimes it is even personal. Paul is like a brother to me, even though we just met. Another one of my pieces of advice at Women 2.0 was “get raw.” It involves making yourself completely vulnerable.

“We had a situation and my gut was like ‘this is all wrong.’ I didn’t want to overreact. I wanted to absorb it and not react period. I wanted to find out more. I reached out to Paul a couple of hours after the situation occurred. I need to ask for your help. I need a gut check. What are your thoughts?

“He was like ‘I feel the same.’ That could have been a situation that got really ugly or I never would have confronted. It would have just festered and gotten really ugly. I went to him right away. I need your help, Paul. It was something with Fanzo. It could have been devastating. We could have just let it slide.

“Other times it is just things like I am not an analytical person, I’m a creative. I can do buzz and I can do a little math. I can put basic charts together, but there are so many times in Powerpoint slide decks that we have to do for investors that I’m just stuck. I can’t do it. So I ask “Can you help me?” Boom, they help. Oh that was easy. Why didn’t I ask for this an hour ago?

“Asking for help can go from the very basic stuff to deeply personal stuff.”

The complete list of advice at the Women 2.0 event was:

    • Keep going
    • Ask for help
    • Trust your gut
    • Get raw
    • Tell your story
    • Forget the haters

Dana expanded on what she shared in my entrepreneuring class:

“Tell your story and be truthful. I love how one of my mentors, Micah Baldwin, has been writing about how you don’t have to talk about how awesome things are and how you’re “Killin’ it!” if that’s not how you’re feeling. In fact, we can relate more to each other when we get vulnerable and more times than not, get the help we need as a result. Yes, it can be incredibly scary but the most beautiful stories are those that touch you because people got raw. Vulnerability translates into stronger, closer relationships. Try it.”

The Myth of Helping

In the Kauffman study on the “Making of a Successful Entrepreneur” most of the factors they studied were assessed by entrepreneurs as being extremely or very important. However, one factor stood out as being not important at all. The figure below shows the responses to how entrepreneurs rated advice from their investors.

My immediate response was surprise. Then I started laughing as I remembered my own reaction to advice from all of our investors and the consulting experts that were forced upon me by our investors. I would always act courteously and listen politely to their advice – and then I would ignore them completely. I wanted the investors’ money but didn’t value the advice.  Neither the investors nor the experts KNEW MY BUSINESS. And I was not about to spend my most precious resource – time – educating them at my expense about my business.

The major observation of my 9MileLabs video ethnography research along with observations at Microsoft and Citrix accelerators is that little communication is occurring – between mentors and entrepreneurs – in either direction.

“Communication is the results that you get, not the words that you speak.” – John Grinder

Before teaching a graduate school class at UW, or mentoring an entrepreneur, or giving a workshop, I take a few minutes to repeat the above advice as a simple mantra. It is a reminder to focus on those I am interacting with and not on what I want to say.

“People need what they need, not what I happen to be best at.” – Author Unknown

Almost every teaching or mentoring interaction starts with me wanting to give my best, forgetting that may not be what the “student” needs. On my best days, I chuckle and back off and remember to do a little human centered design – deeply listening and observing.

Early in the video ethnography study with the nine companies in the 9Mile Labs accelerator Cohort I, this key issue of mentor/entrepreneur communication (or lack thereof) emerged as a research focus. Yet, there was something about this theme that was important and elusive.

From an unexpected place, The Chronicle of Higher Education, came an important insight in a blog post “Mentoring is a Fantasy”:

“Towards the end of grad school, I learned a key lesson about academia. I was discussing a draft of a dissertation chapter with my second reader. Although not my adviser, her work was critical for the arguments that I was building about psychological trauma and technology. Toward the end of the conversation, she said something to the effect of, “You know, this chapter could really use more Heidegger.” Inside, my heart sunk a bit. “Great,” I thought, “more to read. And from an author whose work I don’t really know.” But I dutifully wrote, “More Heidegger,” in the margin of a page, and after the meeting, I checked out a copy of The Question Concerning Technology.

“I read Heidegger and tried to understand how his views on technology fit into his and my larger projects. It wasn’t especially easy going. And perhaps in the third day of thinking about Heidegger, I had an epiphany that was perhaps closer to dasein than technology. As I came to see it, her comments were not so much about the dissertation that I was writing so much as they were about what the dissertation would be if she were writing it. Her comments were built on her wide knowledge of continental philosophy and the fact that she really could have deployed Heidegger effectively in the argument. But it wasn’t reflective of the reality of what I was going to be able to produce at this point in my career. I dropped Heidegger from all but a half sentence in my introduction, and my reader never brought it up again.

“The key lesson that I learned in this interaction is that mentoring is a fantasy, understood in the psychoanalytic sense. When mentors interact with us, their advice frequently comes from a place that reflects what they would do in our situations more than what we can do, given our own specific reality. My adviser had a fantasy version of my dissertation in her head that I simply couldn’t produce. (Her version might very well have been the better version, but that didn’t have much to do with what I was going to write.)

“Importantly, this moment helped me realize not just my mentors’ unrealistic expectations of me but also to see that I often had fantastical expectations of my advisers. The frustration that I felt when I turned in a draft of my first chapter and didn’t have comments within two weeks had everything to do with how I thought the relationship would and should work. Recognizing my expectations as the fantasies they in fact were allowed me to let go of some of what had been hardest for me in the process of writing my dissertation.”

With this insight, we started seeing how little impact the many forms of mentoring were having on the progress of the nine start-up companies. 9Mile Labs had an innovative plan for incorporating mentors into their B2B accelerator:

“We’ve picked the best entrepreneurial, technical, and business minds from the Pacific Northwest and beyond to mentor and coach the 9Mile startups in the program. These mentors aren’t just brilliant, they’re also driven to help propel our startups to the next level.”

The 9Mile Labs partners went further by having several matching processes to link the right mentors with the appropriate start-ups. They even provided financial compensation for the matched mentors. However, the hidden assumption was that the mentors knew how to work with the entrepreneurs and vice versa.

The mentors made recommendations based on how they would do the work, but the entrepreneurs neither knew how to receive the information or what help to ask for in a timely fashion. The entrepreneurs were doing the same thing that I did in my serial entrepreneurial past – do you have some money to invest in my company then I will appear to pay attention to you? If you don’t have money to invest in my company, I will mostly be polite and then completely ignore any advice.

Brant Cooper, author of The Lean Entrepreneur, echoes these observations in “Mentoring Start-ups is Hard: Five Ways to be a Better Mentor.” His five keys to successful mentoring are:

  1. Teach, Don’t Tell
  2. Focus Your Advice
  3. Challenge Assumptions
  4. Beware of Being a Domain Expert
  5. Teach Entrepreneurs how to be Good Mentees

David Robinson, in his book The Seer simplifies the most important part of being a good mentor – provide experience first and make meaning second:

“Effectual entrepreneurs operate from a different mindset than most people; they see through different eyes. This book is intended to shift your mindset so you might see through entrepreneurial eyes. Shifting a mindset is a process, not an intellectual exercise. A dynamic process requires an engagement with the day-to-day experiences of life and, therefore, requires two universal and necessary tools:

 1. Reflective Practice. Processes of self-knowledge are tricky because you are both the subject of the study and the studier. You are attempting to raise your conscious awareness of patterns of thinking and acting. You are sitting on the mountain so you can’t see it. A reflective practice is necessary to see the mountain upon which you sit. In The Artist’s Way this practice was called morning pages. In some processes it is called journaling. In others it goes by the name of reflective writing or free writing. Whatever you wish to call it or however you want to do it, it is an essential tool in opening your eyes to existing patterns and entrenched beliefs. Reflective writing is the best way for you to talk to yourself, to get beyond the moat of what you think you know and discover the deeper story structure driving your actions.

 2. Pattern Breaking. In order to release your grip on what you think you know, to shake up your comfort and control, you need to break habits and patterns and break them intentionally. And, it is better if you have fun doing it. This is the equivalent of the artist’s date. Sometimes this is called stirring the pot, breaking habits, or giving your self a gift. Regardless of the name it is necessary to challenge your assumptions if you want to open your mind and your eyes to new ways of seeing. Breaking patterns will help surface essential bits to write about in your reflective practice. It’s a feedback loop.

“The form of your reflective practice and pattern breaking is less important than the consistency of doing it. Give yourself time to reflect every day so that you may uncover your daily patterns of thinking and seeing. Use the tools, devices, and practices introduced in the book to consciously break your patterns. See what happens. Write about it.”

Experience first; make meaning second.

Yet, there is a foundational issue with mentoring – what is the evidence of credibility of the mentor such that the entrepreneur is interested in listening in the first place. Further, the evidence must be directly and immediately relevant to the entrepreneur. I didn’t understand this until spending time with Paul D’Antilio (formerly COO of GroupTie) when he became CEO of Future Point Systems. He invited me in to share my thoughts on the visual analytics marketplace and what he should do as a CEO.

After fidgeting for an hour while I pontificated on the market and what he should do (violating my mantras above), Paul blurted out “Why should I listen to you? What have you done that makes you an expert? How do I know that Attenex was really successful?”

I was stunned. I thought I’d just been brilliant and enormously helpful and came face to face with Paul “hearing” nothing because of my lack of credibility. I was stuck because I knew that I couldn’t share that the announcement of Attenex being sold to FTI Consulting for $91M was still a month away.

We chatted for a while longer and then I left. I made a note to send Paul the Attenex acquisition announcement. When the deal closed, I sent Paul the press release and he called immediately and said “Now I’m ready to listen.”

Mentoring and being a mentee is indeed hard work. Yet, when the magic happens, there is nothing more rewarding for a mentor than seeing a mentee push forward. For a mentee, there is the gift of knowing that they have a trusted colleague they can turn to whenever needed.

“Communication is the results that you get, not the words that you speak.”

Ed Schein’s Helping: How to Offer, Give and Receive Help describes the challenge of giving and receiving help:

“The most common version of unhelpful help that I have experienced as both helper and client concerns the computer. When I call the help line I often don’t even understand the diagnostic questions that the helper asks me in order to determine what help I need. When my computer coach tells me the several steps I need to take to solve the problem, I don’t know how to interrupt to say, “Wait, I don’t understand the first step.”

“On the other hand, another computer coach I hired asked me what my personal goals were in learning to use the computer, elicited my desire to use it primarily for writing, and then showed me all the programs and tools that would make writing easier. That felt great. Yet when my wife asks me for help with the computer, I routinely fall into the same trap of telling her what I would do, which turns out to be more than she can handle, and we both end up frustrated.”

Schein provides the following principles for helping:

 1. Effective help occurs when both giver and receiver are ready.

 2. Effective help occurs when the helping relationship is perceived to be equitable.

 3. Effective help occurs when the helper is in the proper helping role.

 4. Everything you say or do is an intervention that determines the future of the relationship.

 5. Effective helping starts with pure inquiry.

 6. It is the client who owns the problem.

 7. You never have all the answers.

A Final Word

“What I have tried to do in this short book is to reframe many social processes as variations of “helping.” These include building trust, cooperation, collaboration, teamwork, leadership, and change management. In doing so, I have come to recognize that helping is at the heart of all social life, whether we are talking about ants, birds, or humans. It would seem then that if we can be more effective as helpers, it will improve life for all of us.”

While Schein’s principles are more difficult for the giver, in the end it is more gratifying. I have to remember that the goal is not getting the receiver to take my advice exactly, otherwise they would just be a robot. Rather, the goal is to help both giver and receiver think more deeply about the issues at hand. My way of reminding myself is to remember what epitaph I’d like to have on my tombstone – “He made me think!”

Mikhail, Patrick pointed you in my direction to offer some help. With each email I try my best to follow Schein’s framework. Your gift to me is sharing your journey to becoming an effectual entrepreneur.

Yours in entrepreneuring,

Skip Walter

This entry was posted in Content with Context, Emails to a Young Entrepreneur, Entrepreneuring, Flipped Perspective, Learning. Bookmark the permalink.

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