Sales Leaders Face Challenges of Personal and Company Growth
Cover photo by Mohamed Hassan who can be found here: https://bit.ly/2YTmwiR

Sales Leaders Face Challenges of Personal and Company Growth

This article compiles a number of recent posts on sales, startups, and leadership.


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“What if customers’ single greatest need - is to figure out exactly what they need?”
- Matt Dixon and Brett Anderson

Founders face the same challenges both when building a company and in growing sales.

???????? ????????????????. Avoid the temptation to simply offer what the prospect says they want while ignoring your limits since that leads to disappointment on both sides.

???????????????????? ????????????. Ask difficult questions which go deeper, such as, “What’s your biggest fear with the competition?”

?????? ??????????. Explain how to make their lives better using multiple approaches (e.g. media, cases, charts) since we all learn differently.

???????????? ??????????????. Realize that not everyone should be a client since misalignment wastes time and money. While you may win fewer deals, you will earn trust, longer relationships, and referrals.

?????????????? ??????????????. Strive to know if you impact clients positively. If not, quickly correct any deficiencies and share your learning.

I realize the pressure of cash flow is real. But if your goal is to build something meaningful, invest in knowing yourself and in improving your clients' business. Success will follow.


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"The more you put into it, the more you get out of it" absolutely applies to sales.

How do you grow both revenues and relationships?

??????????????. Apply the Socratic method* by asking questions around goals, timelines, and budgets to draw out big ideas. Then discuss how to visualize and measure success.

??????????????. Offer specific insights, providing a concrete action or maybe an actual gift** (e.g. a new work sample tailored to the prospect). This demonstrates your competence and grasp of their needs.

??????????????. Help them to clearly picture what it will be like to use your product or service. Relate a story or provide a case study to illustrate how a similar customer benefitted.

????????. Ask for feedback along two lines of thinking – the value of your product / service and the merit of your presentation. Use open-ended questions for the best feedback.

????????????. Risk rejection. When it’s clearly a bad fit for now, cut off the deal. This allows you to focus on better opportunities, avoid wasting time, and build long-term trust.

These steps serve your growth as a leader and simultaneously improve your sales process in the long term.

* You can learn more about the Socratic method here: https://bit.ly/3jNUDSU


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Photo by David Blume

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In racing and in sales, you want to win. Know the course and the conditions to maximize your speed. Let’s wave the green flag.

?????????????????????? – Understand the industry, demographics, and target persona. With multiple targets, have a cadence for each of them. Know what you want to accomplish in evert contact. Channel Stephen Covey and "begin with the end in mind". I like this quote:

“People are working harder than ever, but because they lack clarity and vision, they aren’t getting very far. They, in essence, are pushing a rope with all of their might.”

???????????? – Move forward without being annoying. Give time to consider your message by waiting 1-4 days between contacts. If you connect, clarify the best way to communicate going forward.

?????????????????????? – Figure it may take seven or more touchpoints to get a prospect’s attention. In one study, making 12+ contacts performed almost 20% better than eight attempts. (To find the report from the Bridge Group, go here: https://bit.ly/3ksdqng)

Follow up as long as you have something interesting to offer. Prospects may not be open to talk until the need is there, and by then they'll want an immediate solution.

???????????????? – Build a consistent, fast, and productive process. Breakdown each part and test timing, messaging, and approach. Even if you’ve been at this a while, consider a tune up, since even the best race cars need to be maintained.


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If the “Three Bears” tale was about sales, Goldilocks would enjoy Assertive bear's porridge while ignoring the Aggressive and Passive bears. OK, time to run away from this analogy, but here’s the real story. Assertiveness is both confident and forceful. It’s not overbearing because you respect the other person.

???????? ???? ???????????? – Push forward by adding facts and reaching for next steps.

“When can I show you how our product works?”

???? ?????????? ?????????? – Pose tough questions early to screen the right customers and set the tone for later questions.

“When will your team be able to install a solution?”

???????? ?? ?????????? – Assert your business expertise and competence in solving problems.

“Can I show you some great results in companies like yours?”

???????? ???????? – Address any concerns directly and creatively.

“Can we discuss some ideas which will work for both of us?”

???????????? “????” – Consider this reply to "We're all set”:

"If you reviewed what I sent and still feel that way, then you're right" and pause. You may get new insights.

Also, beware that forcing the deal now may result in losing lots of time and money later.

Lean into your customers "just right" for mutual benefit.


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Photo by Pablo Fierro

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Your business may be the best, but there's a chasm between you and potential customers.

How do you best bridge the gap? Try being:

????????????????. Answer these prospect questions clearly: Why would I buy what you're selling? Why should I buy it from you?

????????????. Offer useful insights using common words. No one likes unnecessary eloquence, I mean, fancy words.

??????????????. Use metrics to explain. I shifted from “help you scale quickly” to “5 successful M&A transactions” with great effect.

????????????????????. Use case studies, testimonials, etc. to show similar companies benefitting from your solution.

????????????????. Convey your message through multiple channels (e.g. social, text, emails, etc.) and consider changing approaches. Once, we had someone send a plant as a thank you gift for meeting, and it definitely made an impact.

??????????????. Instead of listing all your features and functions, explain how you can effectively solve clients’ real business problems.

????????????????????. As we learned in the post on cadence*, following up is critical so keep sending useful information.

You may be the best. Now it’s time to reach paying customers.


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Decision-makers are being asked to provide their time, energy, and potentially their reputation. In sales, you’re asking a lot.

Knowing this, what if you give something first? Let’s unwrap this.

???????????? ????????????. Offering something first is a great opener. Envision your reaction when getting even a small gift versus another request.

???????????? ??????????????. We rarely truly see others. While any gift is nice, more meaningful gifts* such as a competitive analysis or insight into their industry involve understanding peoples' needs.

?????????? ????????????????????. Finding the perfect present can be a struggle. (Remember a time shopping for an important person.) When our gift resonates with the client, they will appreciate the gesture.

?????????????? ????????????????. The best gifts reflect not only the receiver, but also the giver. Whether demonstrating competence, creativity, or knowledge, make the gesture display your best.

Any collaboration relies on respect - giving first is a great way to show you appreciate their consideration and effort.

Giving initially and thoughtfully pushes your best and sets the right tone to move forward.

* Gifts can include: (in order of how hard): Jokes or cartoons; articles or podcasts; genuine recognition of someone’s work; industry news or report; specific ideas for their business; professional networking referrals; an actual example service or product e.g. your marketing company designs them a landing page.


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Photo by Fabio Brocceri

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In the legend of Icarus, his father creates wings to escape and warns him to not fly too high or too low. Sadly, he plunges from the sky.*

In the reality of startup sales, if you price too high then customers won’t buy, but price too low and the business won’t grow.

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?????????? – Calculate the COGS, salaries, R&D, overhead, and debt servicing to know what you need. Use this to set minimums.

?????????? – Define price in terms of value and how customers can better operate and grow business. Use this to set maximums.

?????????? – Set tiers of prices (e.g. basis, plus, and premium options) to attract both price and value-driven clients.

???????????? – Offer a selection of different products, features, and/or services at different prices allows customers to confidently decide.

?????? ?????????????? – Recognize that while $9.99 is essentially $10, research shows that lowering price just a little has a huge impact.**

Pricing is both science and art. Avoid Icarus fate by soaring at the perfect height.


* In Greek mythology, Icarus and Daedalus attempt to escape from Crete with wings that Daedalus constructed from feathers and wax. Daedalus warns Icarus to not fly too low, lest the sea's dampness clog his wings, nor too high, lest the sun's heat melt the wax. But Icarus flies too close to the sun and he tumbles from the sky. https://en.wikipedia.org/wiki/Icarus

** According to a study conducted by Kenneth J. Wisniewski from the University of Chicago, when the price of margarine dropped from 71 cents at a local grocery chain to 69 cents, sales jumped by an astounding 222%! Two pennies are worth a lot. https://bit.ly/2OGoAcs


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Two chefs fight over the last orange. Each chef needs the orange for their recipe. After fiery debate, they realize that while one needs the juice, the other requires the rind.

This business school case study makes a point to see all sides in a negotiation. You may be near to closing a significant deal but stuck on a couple negotiating points. Here are some ideas to move forward.

???????? ?????????? – Offer a free trial or sample to demonstrate your value. During the period, reinforce how you can help the client succeed.

???????????????????? ?????????????????? – Lower prices to benefit long-term cash flow (e.g. large volume, multiple-year deal, and upfront payment).

For new offerings, an “early adopter discount” recognizes the buyer's risk while keeping the full price as an anchor.

?????????????? / ?????????????? ?????????????? – Negotiate ways to save costs without badly impacting the client, e.g. quarterly versus monthly reports.

???????????????? ???????????????????????????? – Discount price if the client will help you grow, such as a co-marketing commitment (e.g. case study).

Respect both sides and consider each ingredient to creatively build a long and successful relationship.


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Photo by Ylvers

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I’ve seen too many startups devastated when a few clients yield the majority of profits.

Expanding clients lowers overall risk and sprouts other advantages:

  • ???????????????? – Gain unexpected insights across the company.
  • ?????????????? – Offer something fresh to existing clients.
  • ???????????????? ?????????????????????? – Keep roles growing with new offerings.

However, there are potential costs to revenue diversification:

  • ???????? ???? ?????????????????? – Add expenses from new processes and teams.
  • ???????? ???? ?????????? – Spread attention could lead to inefficiency.
  • ???????????????????? – Challenge your communications to existing clients.

How can you get the best ROI with an expansion initiative?

  • ?????? ???????????? – Focus on a highly specific segment until you demonstrate success.
  • ?????????? ???????? – Check progress and adjust the campaign on a regular basis.
  • ???????? ?????????????? – Rely on external resources for creation and implementation then scale once you get traction.

No customer should represent more than 15% of revenues, ideally much lower. Revenue diversity is complicated, but the risk is fatal.


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While myths are powerful,
they can teach the wrong lessons.

You want to define better sales metrics to meaningfully grow your business, not just follow others.

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Myth: You have to track the same metrics as your competition.

Better: Define metrics based on your vision, not others' plans.

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Myth: You want to focus on favorable results.

Better: Measure activity, results, AND outcomes. If you close a ton of new clients but they churn quickly, then you must re-evaluate.

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Myth: The purpose of data is reporting.

Better: Use data to drive strategic decisions through reports connecting behaviors to desirable outcomes.

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Myth: Compensation should be based on quotas.

Better: Recognize outcomes, collaboration, and initiatives tied to goals (e.g. separately reward BOTH introducing and closing deals).

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Myth: Salespeople thrive in competition.

Better: Encourage employees to outperform their past quarters. When we improve ourselves, everyone around us wins.

Sales metrics are a learning device, and not a scoreboard, which help to optimize success.

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I really want to thank Sanj Sanampudi for his wisdom and passion and for helping me better understand some of these topics. Ideas in this article come from the great book, The Challenger Sale, by Matthew Dixon and Brent Adamson, and from M. Jeffrey Hoffman






??Brian Keltner??

?? Award-Winning Agency Helping Entrepreneurs Get More Clients, Business, & Interviews??Reputation Restoration | Online Reputation Management | Business & Professional Branding | Social Media Management | Gunslinger

10 个月

Benjamin, thanks for sharing!

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Art Gassan

Product Marketer Specializing in Go-To-Market Strategies, Customer Journey, Customer Advocacy and Storytelling

3 年

Found it interesting Benjamin, thanks for sharing it.

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Cristian Iannozzi

I Work With Successful Business Men Who Need Their Physique To Match Their Business Success.

3 年

Very interesting read..

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Josie Daigle

Social Media Manager, Marketer, and Consultant

3 年

Interesting read! Thank you for sharing with all of us

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