On Tuesday, I talked about the importance of coaching – Coaches, Coaching, Coach. Today, I want to build on that with sales call coaching. It’s on my mind as we, as a company, start to leverage a new tool to get better visibility and analytics of our calls. I start with Gong.io’s 9 Data-Driven Call Coaching Habits of Effective Sales Leaders.
First, here are the nine habits:
  1. Coaching by “using” your team
  2. Invest in the “middle of the pack”
  3. Don’t water the garden with a firehose
  4. Establish a coaching cadence
  5. Meet for a team coaching session every Tuesday at 2PM
  6. Recorded calls > live shadowing
  7. Positive reinforcement
  8. Theme du jour
  9. Leverage technology

Of these, I want to point out habits 1, 3, 5, 6, and 8.
  • Coaching by “using” your team. Your team is your best asset to act and react for coaching. Using the team creates a collaborative environment. It enables the team members to coach each other. This creates a sustainable environment where the team acts as just that – a team.
  • Don’t water the garden with a firehose. Odd phrasing, admittedly. However, the habit is recommending focus on parts of the call, not the whole call. Trying to improve on too many facets is ineffective and usually ends up causing calls to degenerate.
  • Meet for a team coaching session every Tuesday at 2PM. If you don’t read the article linked above, know that this doesn’t mean to schedule on Tuesdays at 2PM. Instead, it’s an example of scheduling time on the calendar and making a regular cadence of it. Remember: you make time for the things that matter.
  • Recorded calls > live shadowing. Trying to coach in the middle of a call is good, but similar to garden watering above, sales professionals should be focused on the call. They should not try to adapt on-the-fly. Do the autopsy of the call when it’s over. Adapt for the next.
  • Theme du jour. Focusing energy and improving on skills requires repetition. Thus, it’s important to coach on a specific goal several times in succession. Don’t shift until the goal is effectively achieved or improved upon.

Sales coaching is paramount for our industry to improve and adapt to changing times. As technology makes outreach easier, sales skills will be the differentiator.

My startup’s product gives companies automatic visibility –no added work or key entry from anyone— into their business relationships – everyone involved, the ongoing discussions, meetings occurred and upcoming, and more. We’re built on the premise that transparency yields greater sales results. This shouldn’t be too much of a shock when you consider how teams (sales teams, sports teams, etc.) frequently put communication as the cornerstone of team strategies.
Of course, visibility gives leaders and managers capacity to coach team members. Coaches review game film with players for coaching – pre-game or post. For our customers, it’s enlightening when leadership tout the coaching aspect of our product. For many, it’s a key one benefit they hadn’t thought of, but rises as just as powerful as their original buying intent.
I’ve always been a fan of coaching. Coaching is how players (in any role) get better (+ practice). It’s how C players become B players, B players to A players, and so on.
When was the last time you were coached? Why? Did you ask for it? Did you accept it? What was the outcome?
Heck, reviewing history, especially our “last game” (soccer game, sales call, etc.), enables us to coach ourselves. This was a great point I noticed after reading Inner Game of Tennis. Self-reflection –watching and listening to ourselves– is a fantastic way to coach ourselves.
For the most part, we want to be better versions of ourselves. Sometimes, that means trying harder. Sometimes, that means trying more often. Coaching by a peer, a leader, or ourselves gives us the chance to make whatever effort we use moreeffective.
Look for coaches. Ask for coaching. Be a coach.
I’m reading Marshall Goldsmith’s What Got You’re Here Won’t Get Your There, and early on, Marshall talks about the importance of what gets stopped. We often hear of the successes of others. As Marshall points out, though, there are many reasons why successful people succeed. What is oftentimes just as important (if not more so) and is not talked about is what successful people STOP doing.
What entrepreneurs may stop, for example, is down a path that would not yield successful outcomes. Successful startups are known for their successes; rarely for their failures or what they do to shift their focus.
Marshall writes how people try to change habits and create great processes. This can be challenging, however, with several steps required. Instead, folks could be better off by focusing on small things to STOP doing. Oftentimes, this is just enough to create noticeable, positive results.
When I read all of this, I think about self-awareness, being comfortable with the uncomfortable, and making small changes for sustainable effects. Case in point: I hate vegetables. I really do. However, I realize the importance of eating vegetables for their nutrients. To change this, many people think about the need to make big changes – start eating a lot of vegetables.
For me, I realize what I really want to do is to be open to eating vegetables – not be scared off by them. For me, I’m indeed adding a vegetable a day as part of a “30 Broccoli, 30 Days” challenge – consuming broccoli florets daily for 30 days. I’m not going for a lot because I know me well. Meanwhile, the goal here is not to be a vegetarian or to even start eating a lot of vegetables – that just wouldn’t be me (read: hardly sustainable). Instead, I want to STOP ignoring vegetables on my plate (or throw them away ?).
I want to be a better writer. I realized early on how often I use “so” in my writing. Now, I’m aware of this and am limiting (“stopping”) how often I use the word. I am also working on STOPPING filler words in my speech. I’m not trying to improve how I speak by taking speaking courses or studying a thesaurus. Instead, I’m stopping what I feel is not productive for effective speakers.
Think about yourself. Think about what you want to improve. Think about what you want to STOPrather than what you want to do.
The capitalization table (cap table) is referred to the agreement of shares and ownership of a company. It sits at the intersection of shareholder, number of shares, and company valuation.
I realized that I’ve never touched on this in previous Finance of Startupsposts, so I’ll cover that ground here.
A few examples of cap tables…
Lois and Clark want to cofound a venture to provide virtual tours into the unknown – called The Great Digital Explore. Lois will be the CEO while Clark will be the CTO. Given their differing skill sets and being friends, they’ve decided to split ownership in half – 50-50. They’ve also decided to set aside 20% of the company for future employees. They value the company initially at $20,000. Par value is $0.002 as they “create” an initial pool of 10,00,000 shares (pretty standard).
The cap table for The Great Digital Explore would look like this:
Shareholder
Equity Position
Number of Shares
Price per Share
Value
Lois
40%
4,000,000
$0.002
$8,000
Clark
40%
4,000,000
$0.002
$8,000
Employee Pool
20%
2,000,000
$0.002
$4,000
100%
10,000,000
$0.002
$20,000
Three retired Navy SEALs are looking to start a private security company – Aramis, Athos, Porthos. Being the former team captain while in the SEAL program, Aramis is the CEO, and commands a slightly higher ownership of their new company Musketeer Security Services while Athos and Porthos hold equal positions. As they form, they value their company at $10,000 (with par value of $0.001 at 10,000,000 shares). The three see teamwork to be essential in the success of their company, so they set aside 30% of the company for future employees.
The cap table for Musketeer Security Services would look like this:
Shareholder
Equity Position
Number of Shares
Price per Share
Value
Aramis
28%
2,800,000
$0.001
$2,800
Athos
21%
2,100,000
$0.001
$2,100
Porthos
21%
2,100,000
$0.001
$2,100
Employee Pool
30%
3,000,000
$0.001
$3,000
100%
10,000,000
$0.001
$10,000
As Aramis, Athos, and Porthos are starting up, one of their young SEAL members overhears their discussions. Being the Millennial that he is, D’Artagnan is eager to join the team. He’s fascinated by entrepreneurship. Musketeer Security Services is already up and running, however, and have made a good name for themselves such that they are growing. D’Artagnan wants a piece of the pie and with a sizable bank account from summer jobs when he was younger, he wants to not only join as an employee, but he wants to contribute to the bank. D’Artagnan wishes to inject $100,000 (pizza delivery was very good business for four summers). They all agree on a pre-money valuation of $750,000.
Let’s see how this shakes up the cap table:
(Remember, $750,000 for the pre-money value divided by 10,000,000 shares = $0.075 par value.)
Shareholder
Equity Position
Number of Shares
Price per Share
Value
Aramis
24.7%
2,800,000
$0.075
$210,000
Athos
18.5%
2,100,000
$0.075
$157,500
Porthos
18.5%
2,100,000
$0.075
$157,500
D’Artagnan
11.7%
1,333,333
$0.075
$100,000
Employee Pool
26.5%
3,000,000
$0.075
$225,000
100%
10,000,000
$0.001
$850,000
This isn’t too complicated. It will get complicated as investors start pouring in capital with varying stock classes – common, preferred, etc. You can check out the prior posts to see how the cap table is affected by those capital raises – Finance of Startups.
Empathy. It’s been on my mind a lot recently, and I’m trying to understand why. Then, it hit me – too often we lack it, and this leaves others (most everyone) feeling isolated.
Merriam-Webster’s dictionary defines empathy as:

The ability to understand and share the feelings of another.

I’ve decided to dedicate today’s post to this singular word because it’s highly important for not just everyday citizens of our communities, but also as entrepreneurs. If you can’t be empathetic to your customers’ problems, you’ll likely fail to build a product/ service that resonates and is sustainable.
First, sympathy and empathy are not the same. It’s important to know the difference because they’re oftentimes interchanged improperly. Sympathy is defined as feelings of pity and sorrow for someone else’s misfortune, or understanding between people; common feeling. Empathy goes deeper than sympathy in being able to share/ experience emotions of another.
In a recent enlightenment of empathy and the lack thereof, I took on a recent challenge – calling it “30 broccoli, 30 days”. I loathe vegetables. I haven’t touched broccoli in many, many years prior to this challenge (started September 1st). The challenge is to consume at least one broccoli a day. Since, I’ve decided to ramp up the number of broccoli florets each week.
The funny thing here is you may be reading this and asking, “so what? It’s just a single floret.” Therein lies the problem. Where your mind takes you next is where empathy either surfaces, or not. I’ve indeed received many people asking the same question including the occasional ridicule. Though I’m not so bothered about this because I understand why, I’m also coming to the realization how often others fail to understand my why. It’s shocking how often people jump to conclusions based on how they feel and what they think. There is no compassion or interest in learning my perspective.
This lack of empathy reared its ugly head during 100 Strangers, 100 Days. Too often, people judge from the outside, and set all subsequent interactions based on this judgement. There is a lack of interest in getting to know others – the good and the bad.
Truth is, consuming broccoli is akin to my own mini-Fear Factor. Perhaps I’m sharing this to practice vulnerability knowing full well there are those who will ridicule. That’s okay. I’m confronting my fear because I do know vegetables are “good” for me, though, I loathe them. So, I challenge myself.
How often do others confront their fears? How often do others look for ways to challenge themselves? That’s okay, too. Truth here, too, is that I do my thing because I know my why and I know what I want to achieve. Do others feel the same way about themselves? I’m not sure, and it doesn’t matter. It shouldn’t in this case. But I’m happy to learn.
Take a moment today, tomorrow, this week. Practice a little empathy. If you feel the knee-jerk reaction to judge and ridicule, fine. But then, follow up those thoughts with questions of why.
Empathy might be that one big thing we’re missing in our communities that’s driving wild accusations and creating misunderstood resentment. Practice empathy.
Last week, I shared a post about negative churn – when revenue from existing customers is greater than revenue lost from customers churning (see article). The relevant question, then, is how do companies achieve negative churn? Here are a few options:
  • Additional licenses – This one is common in today’s SaaS companies – selling based on licenses or “seats”. As a team grows, more seats may be required to gain access to a product/ service. 
  • Cross-sell – This type of sale captures cross-functionally opportunities within an organization. For example, a CRM may first be sold to a sales team to manage pipeline. Then, marketing may buy access to the CRM to understand lead and prospect-flow. And so on…
  • Up-sell –Many products and services have tiered business models (packages). Tiered packages allow for companies to address a market’s consumer surplus – sell packages that capitalize on differing price considerations, typically. Think: silver, gold, platinum packages with options that are locked for specific packages.
  • Additional products/ services – Up-selling largely occurs with tiered packages. However, packages are typically within the same product. This sell-on type is about selling a different product/ service. These tend to be complementary offers. For example, a product seller may sell professional services. This can also include things like accessories or service plans (think: cellphone cases or insurance plans).

There are many ways for businesses to continue to sell to existing customers – plenty of latitude to supplement the company’s business model. These are the opportunities that give investors excitement to grow a market beyond its existing.

I met an entrepreneur recently who is approaching a similar market and product that I once did. Before meeting, he realized I had written a book, so read it beforehand. It resonated greatly for him. As we met, he had a few specific questions including: “if you could do it all over again, what would you change?”
There was a lot I would change as I’ve outlined on this blog and in Postmortem of a Failed Startup: Lessons for Success. There are always ways to improve. But one major lesson stuck out at me – start out smaller, more deliberate. Start out with a very specific product addressing a very specific pain.
This would invariably lead to quicker rollout of the product. This would lead to quicker feedback. This would lead to quicker iterations. This would lead to… success? I’m not sure, but I feel this approach would have been much smarter.
Success does not follow a formula. The most brilliant minds have failed. It’s critical to fail at times, too. But the approach to success can be tuned in to mitigate risk. I think my big take-aways after all these years also line up with being loved by customers (the product, at first) to create something wanted… needed. With that, I want to tackle opportunities with a focused effort and building something that enables my customers that also aligns with my vision in mind.
Looking back at your ventures, what would you do different?
Negative churn – a major milestone for any company. Negative churn occurs when the growth of revenue offsets the loss of revenue from customers who leave (churn). This is a great metric for SaaS companies, especially.
Churn, if you recall, is the rate of loss of customers (leave). Just about every company will experience loss of customers in recurring revenue companies.
In effect, companies who have negative churn can continue to grow without having to sign any new customers (at least, short-term). That is a remarkable milestone, and one that is highly valued by investors. It points to growth opportunities with up-sell and cross-sell opportunities as well as high retention. It points to a loved company and its products.
Achieve low churn. Then, aim for negative churn.