I’ve been reading a lot about customer success and onboarding recently. It’s top of mind for me these days as we continue to onboard more and more customers at SalesWise. Two articles that have stood out: 

The Slack article was more about go-to-market strategy. In it were important tenets that were also echoed by WP Curve. This includes the importance of getting to the “wow” factor.
I wrote a post before titled “U in UX Stands for You: The Evolution of Consumer Engagement”. I highlighted the importance of early user experience like Spotify which enables users to get up and running quickly. Then, I highlighted the importance of empty-state design in “Starting With Nothing: Solving Early Churn With Empty State Design”.
After reading the WP Curve and Slack articles about the “wow” factor, it’s important today more than ever to present value immediately. For Slack, the “wow” moment was user engagement. For Spotify, it was signing up and browsing channels before listening. For a marketing automation platform, it’s seeing an automated campaign in action.
At SalesWise, many customers share their “wow” moment — getting real-time visibility into insightful data they hadn’t seen before. We do this with simple, secure Oauth for services like Gmail and Salesforce. In 10 minutes, an entire company can be up and running. The algorithms and heuristics work in the background to organize it all. That’s how we get to “wow” fast.
One President of a customer company said it simply: “You deliver on the SaaS promise”. That is, our platform just worked. Some customers share how other SaaS platforms they started trials with took too much effort to set up. Even in today’s world of SaaS and APIs, set-up friction is high.
Body Boss, back in the day, required too much effort to get to the “wow”. We required too much setup of strength coaches. Thus, we had many coaches bail after the first and second visits.
It’s critical for companies to recognize “wow” moments, and how to deliver that as soon as a user signs up. The SalesWise “wow” factor is seeing real-time sales activities automatically organized. We’re developing some new features that will highlight even more “wow”. We’ll be able to help our customers instantly identify sales opportunities that may fall through the cracks. This will drive immediate value by spurring a sales rep to take action. This, in itself, will be massive in value to our customers.
Find your “wow” factor, and deliver it as soon as possible. Find ways to present value and insights without having to do much set up. Show enough to get the user to get value. You can always get more data and do more set up once the user sees immediate value.
In 1914, Ernest Shackleton wrote a job posting for his ship’s crew members for his voyage to Antarctica. It read something like this –
(photo cred: http://seamlessbrand.blogspot.com/2011/01/hiring-like-shackleton.html)
Ernest received over 5,000 applicants, and eventually hired 26 men (+1 stowaway) for his voyage to the icy continent.
The incredible part of this story isn’t how many applicants would wantingly apply. Instead, it’s that the ship never made it to Antarctica. 10 months after setting out, the waters around the ship turned to ice, trapping the ship and its crew. The crew split to seek help, and extraordinarily, all 27 crew members survived and made it back two years after they launched! That’s incredible.
I bring this up as the follow-up to my last post — Interviewing 101 – No Hypotheticals and Go Deeper. Having read the Shackleton story (“Endurance”) in Simon Sinek’s Start With Why, I’m integrating a similar idea in my hiring process.
Sales is hard. It takes 6-8 touches to reach a prospect these days. That number has potential to grow given the number of sales tools in the market. Read: there’s a lot of noise to get a prospect’s attention.
Also, working at a startup is hard. You wear many hats, and you can work long into the night and on the weekends. Success isn’t guaranteed. It’s not as glamorous as others make it out to be.
Couple sales at a startup, and the intensity and difficulty amplify. As a sales rep, you’re challenged with prospects’ uneasiness of viability of the company, low brand recognition, a nascent product (or you have a substitutable product in a highly competitive space), etc. You don’t have the benefit of marketing and sales ops teams tinkering to make success even more successful. Maybe the startup hasn’t even hit product-market fit… It’s tough.
In terms of sales, working at an early startup can be akin to traversing to Antarctica in 1914. To that point, I want to dig into what drives candidates. Why do them want to be a sales rep at a startup? I want to know if the candidate is financially motivated. I want to know if the candidate is purpose motivated. I want to know if the candidate is competition motivated. Does the candidate hope to use this experience to build her own startup one day? I want to know the candidate can not only can handle the pressure and the difficulty, but I want to know she wantsto. Does she embrace the challenge?
The key to all this, too, isn’t just about hiring and finding someone who will be a sales rock star for the company. The co-key, if you will, is being a company where the candidate will be successful. A candidate is investing his time and energy with us. The candidate could be forgoing higher pay and simple life. Burning out or leaving after 3 months is not good for any of us. The candidate will be an integral part of the team. When I hire, it’s not just about company. It’s about the candidate. It’s about how we, as a company can help the candidate achieve his WHY and his PURPOSE. It’s about how I can enable him to be successful.
When hiring, I’m trying an approach from 100 Strangers, 100 Days – to go deeper with proceeding questions. I start out with one question, and I ask follow-on questions that probe deeper. I do this to, hopefully, mitigate the candidate telling me what I “want” to hear.
I sat down with one of my sales coaches recently about his hiring strategy. He told me to never ask “hypotheticals.” He and I realize how easy it is for candidates to serve up an answer that we want to hear. An example of a hypothetical: “Tell me how you would handle a rejection.”
Similarly, simply asking the candidate to share a real experience without probing deeper can be misleading – “tell me how you have handled a lost deal – one that you had been working for months.” It’s too easy for candidates to serve up a similarly “wanted” answer. It’s important to dive at least 3 layers deeper with follow-on questions. You can even use the 5 Whys strategy.
In 100 Strangers, 100 Days, I started out asking the similar questions to each Stranger, but I felt the conversation really was like an interview, and it was difficult to determine the authenticity of responses. Meanwhile, I felt my meets with Strangers were very… sterile (“un-engaging”). After altering my  approach by asking a single question, and then asking follow-on questions based on the Stranger’s response, I felt Strangers really opened up. Our conversation flowed much smoother which enabled the Stranger to open up even more about all topics.
Asking follow-on questions coupled with explicit questions from his/ her experience allows you to drive down into what’s real beyond the original “sugar-coated” responses. This is a similar approach to sales. Successful sales approaches go beyond an initial response to get down to root causes and challenges.
It’s up to the interviewer to know how to poke and prod to get to answer s/he’s looking for – be it a skill, value, mission, other.
When interviewing or trying to sell, stay away from hypotheticals, and go beyond the first question. Build from the first question layers deeper.
For me, entrepreneurship is a game. It’s a game where the odds are heavily stacked against my team and me. As I sit down here on a Saturday afternoon at Starbucks typing out my blog post for Thursday (published today), I realize that I’m doing something unconventional for most. It’s all for the love of the game.
This morning, I played a good, healthy game of pick-up soccer with friends. This afternoon, I challenged my mind in a more mindful way with meditation. Tomorrow morning, I will go to the gym and grimace and fight against some iron. Other than that, I’ll likely get a good bit of “work” in. I put work in quotes because to me, it’s actually a game, a sport for my mind.
I’ve chosen this life to work at a startup, to be entrepreneurial, to read and to write because I love the challenge of it all. These challenges are like sports, but for my mind.
As it pertains to Entrepreneurial Ninja (this blog), it’s my way of learning and teaching myself. The competitive aspect is to be a better self – to always learn and improve. It’s to be consistent. I’m playing against, perhaps, my favorite opponent – myself.
I love challenging myself to do things I found uncomfortable years before. I love saying that I’m building a new sales process or creating the new marketing strategy on a day and an hour where others aren’t. I love getting up to work out early in the morning or go lift even when sick because I know most others wouldn’t, and I aim to be the best.
So, today in this startup, I consider this all a game. I want to win. Stats say 90% of startups won’t be “successful”, but I love that, too. I love looking into the mirror, and saying, “look at what I’m about to do”. I’ve come here to win with my team. I’ve come here to build something great. Yes, there’s the mission to provide jobs for others and to create a loved brand, but make no mistake – I love playing the game… love for the entrepreneurial game.
Why are you doing what you do?
Lesson #20 from last week’s post 24 Lessons I Learned from Meeting 100 Strangers Over 100 Days had a subtle “opportunity” moving forward, not necessarily a lesson – the role of perspectives.
I debated making this the 25th lesson. I believe there are other ways to slice outcomes from journeys such as #100Strangers100Days by looking at what the journey enables moving forward. Like reading a book and sharing take-aways, one can gain perspective from a journey.  
Perspectives enable…
  • Understanding and empathy. Instead of asking how could someone vote for XYZ candidate, and asking in a negative, shocking way, consider the same question with intrigue. Ask to find out why – did you miss some valid point? Instead of jumping to a judgement, ask to learn why.
  • Expertise.You can gain a deeper perspective in your field. You can read a host of books that support your research. You can go on a journey to meet 10 Strangers to help you cope with social anxiety. You can deepen your knowledge, and become an expert.
  • Adaptability.Adaptability, athleticism, fungibility… all words one of my former bosses said all the time to me when recruiting. Now, those words are some of my favorite. I’ve taken them to heart. I hear often from others who struggle to translate prior experience to some amazing job opening. Well, many lessons and examples from your experience, the interactions, the best practices, you can port to new companies. Perspectives allow you to adapt and apply a possibly foreign concept in a new, novel way.  
  • Some kick-ass conversations. This one was for fun, but so true. Perspectives can bring about change. Perspectives can bring fun and laughter. Perspectives can lessen burdens.

Perspectives can shape the way you think about otherwise static thinking. Perspectives can open opportunities from “completely” different worlds. The beauty, too, is that perspectives just take curiosity and patience.

(Deep, right? I know. I can hit that note every once in a while.)
I received a question recently from an entrepreneur about working part-time/ contract work as her startup continues to build momentum. She wasn’t sure how to talk about her company with potential head hunters. Head hunters advised her that employers could view her startup as a “conflict of interest”.
In the employers’ minds, the entrepreneur would be “taking advantage” of the company. The entrepreneur (read: “worker”) would be taking a higher rate, and leaving soon to work on her company.
My response is that there’s no “advantage” here. Instead, there’s mutually beneficial relationship. 
Some quick thoughts on this:
  • The employer is hiring a part-time/ contractor for flexibility and expertise. The employer does not have to pay for benefits, taxes (in most cases), and any severance packages. Meanwhile, the employer gets a skilled resource to address an exact business problem. It’s an beneficial arrangement for both parties.
  • A clear scope of work and deliverables ensures the entrepreneur is meeting expectations. It’s up to both parties if those expectations are exceeded (or not).
  • The entrepreneur should be upfront in her passions and what she wants to do. There is not a finite period of work at this point. It’s up to both parties to find a mutually beneficial arrangement. Again, the employer is looking for part-time/ contractor work anyways.
  • Big companies do, in fact, value entrepreneurial mindsets. These days, companies of all sizes realize the potential of more agile competitors. As such, companies are looking for capable, creative, and ambitious resources. These resources enable agility for companies.
  • Cultural fit is key. The right companies will realize fit with the entrepreneur, and vice versa. Some companies will leverage the entrepreneurial skills to bring a new product to market. Others may want the worker to augment a team and execute. In any case, it’s down to people on both sides to enable growth on both sides.

Entrepreneurial ventures can enable some of the best experience anyone can ever have. Through entrepreneurship, founders can learn all facets of the business with a real-world MBA. They’ll learn through the ups and downs of why corporations operate today. (Corporations exist and create structure to scale early success, after all.) For the entrepreneur, be confident and honest with what you’ve done. Be honest with what you want to achieve. Realize the right opportunity will enable both parties to benefit.

There are so many ways to cut my lessons learned from 100 Strangers, 100 Days. Today, I’m going to give you a slice of the grander, big-picture lessons. I’ve written 24. Yes, that’s a lot. However, I probably could’ve written a hundred, and indeed, I thought about it. However, that’d be overkill, and you likely wouldn’t read it anyways.

So, here are 24. 24 because… that’s just where I decided to draw the line. Enjoy them, but please… learn some lessons on your own, too. J
  1. It doesn’t take much to start something important to you. I came up with theidea for 100 Strangers, 100 Days while hiking one Saturday morning in September. Within two hours, I interviewed my first Stranger. Within six hours, I had 100Strangers100Days.comup and running. It doesn’t take much to start, and get something off the ground. Just takes focus and commitment.
  2. It takes a lot to be consistent. The hardest part of the journey was not meeting Strangers. It was meeting one and writing about the interaction each day for 100 days. Some days, I wasn’t feeling up for it. However, I did it because that’s what this journey was about. Being consistent. Being deliberate. Meeting people. This is what separates the true doers from the wanters – executing.
  3. You can meet people everywhere. I walked up to Strangers with familiar faces around the office, Starbucks, and yoga, primarily. However, I also met complete Strangers in these places plus while shopping, walking on the street, hiking Stone Mountain, in line for a restaurant in Boston, everywhere. Meeting new faces is not as hard as many believe. Couple this with explicit networking events, and you can meet like-minded people and build new and existing circles.
  4. Things may always be awkward, but you’ll be comfortable about it. I was pretty natural, I think, at the beginning. However, I was still uncomfortable and anxious walking up to complete Strangers to ask them to share their stories with me. That was true up to Day 100. However, I only need to be confident and happy with what I’ve done, so far, for many of those feelings to melt away, and even give light to excitement. I wholeheartedly believe I can walk up to anyone today, and strike up a conversation.
  5. Each opportunity has one thing in common – you. Even when I got rejected, the next person was a new opportunity. I remember being rejected three times in one day before finding a Stranger to talk to me. But each subsequent Stranger knew nothing about the person before rejecting me. I was the only person who knew. It’s important to know what happened, but to keep positive and keep authentic with each Stranger. Think about that if you’re in sales.
  6. People want authenticity. By the end, I had a near 80% acceptance rate. More than half of those who turned me down either because they didn’t have time, or just weren’t open for the picture to be taken. Otherwise, people were very open to just talking to me and sharing their stories. I approached many Strangers who were staring at their phones or working on their computers. Yet, they allowed me to interrupt them, and many smiled as I shared my journey and asked them to be the Stranger of the Day. All of them smiled at the end of our meets.
  7. Support comes in many forms. I had several friends share my journey on their many different social media accounts, and one friend who helped me troubleshoot my website when it went down a few times. Then, I had friends who would ask me questions about how it’s going, but weren’t open to sharing with their friends publicly. There are segments of support in almost everything you do. Know who they are.
  8. Some of the closest people are the most skeptical. I was surprised I was still surprised at this. That is, when I shared #100Strangers100Days with some family and friends, they laughed at the journey with heavy doses of skepticism. They were more skeptical and teasing of the journey than others. Again, realize the segments of support.
  9. Familiarity makes everything so much easier. I did meet a lot of Strangers who I had seen before, but never spoke to, or gotten to know, them. This made introductions, obviously, much easier. Some of these Strangers with familiar faces, I’ve seen for years. I can go on forever, probably, and never say hello to these people because maybe too much time has elapsed that it’d be “awkward”. However, being late is better than never. In fact, it can help break the ice with some laughter – “so after four years of seeing each other, I’ve decided you’re safe to meet!”
  10. It can be hard to be a good listener. Sometimes, my head was running with what else was happening around my life that even listening to the Stranger in front of me for 10 minutes was hard. Couple that with the nature of this journey, I had trouble at times listening to connect and understand. I was listening to respond/ react. This made me, at times, want to interrupt. Be careful if you’re not listening and truly connecting. (I became more conscious when a Stranger mentioned how interrupting others can create silent, negative behaviors long term.)
  11. We don’t see ourselves as beautiful as others do. I took hundreds of pictures of Strangers – several takes for some. I found many takes to be great the first time, but the Strangers would laugh awkwardly and tell me they thought they were ugly. Meanwhile, I took many candid pictures by snapping pictures while they laughed or looked around. Despite many Strangers posing for the camera, these same Strangers wanted me to share their candids.
  12. Not a lot of people think about who they are, or what drives them. A lot of people paused for long moments when I asked them, “Who are you?” Many admitted they didn’t know, and had to think hard. Meanwhile, I had Strangers talk to me days after our meet to share they thought more about the question. It’s interesting how people describe who they are by what they do for work or their relationship status – typically, modes that are extrinsically influenced.
  13. It’s not rambling, it’s sharing a passion. I remember running into a Stranger weeks after we met, and he felt that he rambled on during our meet. I told him that’s not how I felt at all. Whenever someone put me on a path and carried it, I liked that a lot. They shared what was on their mind, and in many cases, they shared their passion. Their excitement helped spur a little bit of a monologue, but that was a great thing to hear. Not everyone allows his/ herself to have a passionate monologue.
  14. You’ll never be yourself as long as you’re being what everyone wants you to be. A recurring theme I heard from others, and one that I lived the premise of through this journey, was being comfortable with who we are. There were Strangers who kept their passions from loved ones because they didn’t believe friends and family would appreciate the passions like they did. Meanwhile, as I mentioned above, I had my own skeptics from friends and family. If I was truly worried about what others thought of this journey, I probably would’ve stopped this long ago, let alone not started. Don’t be like everyone. Don’t mind whatever “weird” is. Be yourself. 
  15. People are acutely interested in whatever true happiness is. I asked the Stranger of the Day if s/he could ask anyone anything (effectively, the next day’s Stranger), what would s/he ask the Stranger? A very common question was what happiness meant, and what was “true” happiness. I’m not sure why that was so common. Was it because they wanted others to think happy thoughts? Was it because they weren’t sure what made them happy? Were they looking for inspiration for what happiness reallyis? A question for another Stranger. J
  16. People just need moments. People need moments to connect. People need moments to escape. People need moments to get in gear to talk about themselves – what drives them. People need a few minutes to set the day-to-day aside. It doesn’t take long or need extraordinary effort to do something or to achieve a smile. It just takes one moment.
  17. Every meeting was just a snapshot in time. Important to recognize we’re all dealing with different things at any given time. I remember a couple Strangers who shared how you never know how others are really doing. Being nice requires no money or skill. Opening a door with a big smile can transmit energy. Someone might have just sold an important life memento of a loved one while burying a best friend. Take a moment. Live in the present. And recognize the power of a single connection right now.
  18. Look up and connect. Over time, the journey became more engaging. Yes, I got better at the approach, but really, our conversations started to flow as my style evolved. At the beginning, I took notes with a pen and paper and a bank of questions. Over time, I stopped asking set questions except for the first question – “Who are you?” Then, I let the conversation flow from there. I then used a voice recorder, so I can look up during our entire interaction, and let the conversation flow. Readers recognized this shift, and responded accordingly telling me how the stories were much funnier, more engaging, and just flowed so much nicer. Let this be a lesson as you’re around others and you have that itch to look down at your phone.
  19. Small goals can work against your much grander goals. Goals are a funny thing much like a Stranger once told me about reaching goals. I kept my eye on Day 100. By doing so, I also had “pocket” Strangers – referring to something like a “pocket veto”. In this case, I knew there were Strangers around that I had seen enough that breaking the ice and engaging them would be really easy. With that, I wouldn’t meet them unless I knew I may have a “difficult” day coming up – like, I would be extremely busy, or would not see as many people. So, I saved these Strangers for difficult days, just in case. What this really did was give me too much comfort and delayed the grander ambition to make connections. Be aware of those goals and those metrics you measure.
  20. Get to know people to break biases and judgements. I caught myself a couple times looking at someone and making a snap judgement. When I realized I made a negative judgement, I told myself to go ask that person to be the Stranger of the Day. I wanted to force myself to get to know people, and beware of snap judgements. Each time I did this, I discovered something great about the person.
  21. People think you need a novel concept to start something. You don’t. A lot of people (friends and Strangers) were amazed by this journey. They were inquisitive about how this journey came about. They were fascinated about the stories. They then thought they couldn’t do it, or they could never think of a journey like this. Here’s the thing – meeting Strangers is not novel. Writing about them is not novel. I just wrapped it all up in a package, and did it. It’s almost always about execution, not the idea.
  22. Each connection is a connection that can change lives. I had several friends who read about a Stranger they had seen before, and then, they actually went to meet the Stranger. They used the Stranger story as a foot in the door to get to know the Stranger even better. I’ve even connected some because of business synergies. The most obvious connections are sometimes hidden in plain sight.
  23. People are great. People are beautiful. You can connect with anyone. To the point above, we all have some amazing story somewhere in us. The people around us are not that strange after all. The people around us are not as foreign after all. We are all connected in some way, and you’ll find that when you take a moment and say hello, and go beyond the hello.
  24. You’re sometimes never really ready, but you kind of assimilate to whatever success looks like just by doing. This lesson kind of wraps up a lot of the entrepreneurial lessons above. That is, the level of effort I put into this was a lot more than I originally thought. Had I known this, I’m not sure I would’ve started. I was nervous walking up to some Strangers, but once I put my feet together or said hello, there was no turning back. Sometimes, the best thing you can do is to fire before you ready yourself and aim. Happily, I’ve found I’m pretty good at this whole make-it-up-as-I-go-along-and-learn-and-adapt thing. Just go.

“There are no strangers here; Only friends you haven’t yet met.” – William Butler Yeats

I’ve always been a big proponent that you make time for the things and people that matter. Sounds simple, right? Then, why do so many not implement this better in their lives? Let me take a moment to recognize this more explicitly.
I touched on Laura Vanderkam’s TED Talk “How to Gain Control of Your Free Time” in last week’s post. In it, she shares a story of a woman who had a leak in her home. Coordinating with plumbers, and getting everything resolved, the woman estimated that it probably took seven hours of attention. That’s seven hours of “stuff” the woman hadn’t planned on doing. If you were to ask her (or most anyone) to find seven hours in the week before, she’d have told you, “heck, no, I don’t have seven hours. I’m busy!”
I was thinking of Laura’s talk in conjunction with Jacob Christensen’s How Will You Measure Your Life. Specifically, I’m aligning “making time” with Christensen’s Resources-Processes-Priorities framework. We make (process) time (resources) for the things that matter (priorities). From Christensen:

“Resources are what he uses to do it, processes are how he does it, and priorities are why he does it.”

I wrapped up 100 Strangers, 100 Days last week. Wow, that took a little more time than I thought. Meeting a Stranger was about 1.5 hours all in including:
  • 10-15 minutes “interviewing” 
  • + 15 minutes post-meet (many Strangers wanted to talk more and ask questions about the journey) 
  • + 60 minutes to transcribe our meet + social media updates (and formatting). 

It’s a lot, and I did that every day for 100 Days on top of the large workload I already do as the Head of Sales and Marketing at an early-stage startup. However, I managed to do it by setting each meet as a high priority of my day. I cut back on the lower priority items. Meanwhile, I also focused energy on the other facets of my life important to me – family, friends, working out, etc. Read: I was much more deliberate in my actions and the time I spent (and with whom).

Once you cut out the noise and the things that distract you, it’s amazing how much time you’ll find. Or rather, it’s amazing the quality of your life improves when you make time for the people and things that matter. 
It’s been a little over a week since I wrapped up #100Strangers100Days, and I’ve given this a little reflection. As you can imagine, I get a lot of questions on what’s next and what my lessons have been. I find the question for lessons learned interesting.
When I think about lessons we learn, we learn them because they somehow resonate with us. They resonate with us so we can remember them. When I create my list of lessons learned, they will be my own.
I’m wondering how many people will try to learn their own lessons, or are they looking to me for the Cliff’s Notes. Meeting the 100 Strangers required no patented process. Required no money. Demanded little time. (What took a lot of time was everything after the meet.) Anyone can do this.
Again, the lessons will be my own, and though, I might paint them in a light that is best seen and understood by others, they will be mine.
Meeting a handful of Strangers today, tomorrow, over the next two weeks, and learning from the experience (and maybe making some great connections), just requires an initiative. Then, those lessons will be your own. Don’t need to blog about them. Don’t need to bust out a voice recorder. Don’t need to start with “Who are you?” Instead, your lessons and journey starts today, and you can take whatever path you wish.
(This is true beyond meeting Strangers, too.)