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Improving Sales Experiences in an Unpredictable World

SES Boston - Driving Sales Experience: Moving to Hybrid

The Boston Chapter of the Sales Enablement Society met in. June of 2021 to discuss the sales experiences in a world still reeling from Covid-19. We have continued to enhance this as the world changes around us without losing sight of where this conversation began.

This article will cover those original ideas, fleshing out as we go and evolving to match the ever-changing world around us. Sales skills have always needed to keep up with the universe around it, and how we help our sales team do so will change.

This article follows the following path:

  • Where did our conversation come from?
  • What were our initial takeaways in June of 2021?
  • Best practices for driving unique sales experiences now

First, where did this conversation on sales experiences begin

Our conversation began from a LinkedIn post from Corey Kossack where he noted:


We’ll see more salespeople poached from their company this year than any year in the last decade.

They’ll move for more money, flexibility or purpose.

And 50% of those who jump ship will do it again within 12 months.

It’s going to be a messy next 18 months for companies, and especially for sales organizations.

Employee retention rate should be the North Star metric between now and the end of 2022.”

We started down this path of seller engagement by focusing this first meeting on how the shift to hybrid working models is and will continue to impact the experience of the sales manager, individual sales reps, and the entire organization.. As we explored the topic, we primarily viewed it from the following perspectives:

  • The war for talent
  • The risk of creating inequity in your sales force.

The world of hybrid boils down to trust between managers and employees, businesses and employees. From trust comes responsibility, and more trust is given from delivering results based upon the responsibilities given. It is a virtuous cycle for the business, the manager, and the employee.

Our initial conclusions

The war for talent is underway

Over the last year, employees have tasted what it is like to integrate life and work more deeply, to have more flexibility in getting their jobs done. Those that have shown personal motivation have earned more responsibility and trust, and they do not want to go back to pre-pandemic working models.

Sales management that forces sellers into old working models will be left behind, giving up on the understanding, trust, and flexibility that today’s workers have become accustomed to.  

Your best employees will leave for better experiences and opportunities.

And, it’s expensive when you lose sellers. Data from SiriusDecisions estimates that the cost of seller turnover is around $200,000, between lost opportunity cost, retraining, hiring, and so forth.

Your costs will vary, of course, but will likely be on the order of $100,000 to $500,000. 

It is never cheap.

How can your enablement team help?

  • Educate managers on how to care for individuals based upon coaching the whole person.
  • Partner with Ops and Managers on data analysis to identify who is getting the work done and who is not.  
  • Some salespeople expressed the importance of autonomy and mastery (Daniel Pink research) over rewards and recognition. One of our fellow Enablement practitioners noted that they have had success having people “qualify for an advanced training instead of receiving a reward.” Consider this for your business.

Moving to Hybrid Risk – Remote employees becoming the forgotten and unheard

Participants noted that many people returning to the office had forgotten the remote participants in meetings, talking over each other and forgetting the impact on those not in the room.

What role can Enablement, and frankly others, play?

  • Remember WIIFM (what’s in it for me) and ensure that all meeting participants, in person or remote, continue to see the promise of WIIFM.
  • Building off of the last point, commit to standing up for the forgotten. This expectation goes well beyond a hybrid working model. Use your voice, and put into action, what is needed to ensure all voices are heard and that your business focuses on creating great experiences for all sellers, not just certain ones.
  • Work with the team to create best practices around how to work effectively with all groups. For example:
    • Validate those critical areas of the room are visible to all.
    • Ensure background noise issues are kept to a minimum.
    • Formalize the meeting flow to ensure time is available for remote employees to participate/comment without having to scream to be heard.
    • Partner with HR and representatives from in-person, remote, and hybrid workers to represent all voices.
    • For training, Instructors need support to manage the environment (monitor chat, help with breakouts, etc.); you can see the difference when companies bring in a team vs. a single instructor; this will only be more pronounced moving to hybrid.
  • Work harder to have remote coffee or lunch with those people, even a five-minute call. Support the team in creating these connections.
  • Build-in time for remote and in-person employees to meet in person 2-4 times a year (at minimum). The value of these in-person meetings will enable the building of stronger relationships faster.

Best Practices for Better Sales Experiences

Customers that work with unhappy sellers will feel that unhappiness.

You need to ensure, from your hiring and onboarding, through their entire career in your business that all employees, your customers, and others feel that they are working with an organization that delivers positive outcomes and great experiences wherever possible.

I won’t harp on that point; let’s dig in on sales experiences.

It starts right at the beginning

Make sure you are crystal clear in the job description of who you are looking to hire.

The interview needs to be great on both sides.

From the moment the hiring manager begins the job interview, the tone is set. So set the stage right.

Ensure every member of the interview team:

  • Understand what they are looking for in terms of previous experience, critical skills, competencies, etc.
  • Have the skills needed to interview; too often, people are thrown together with little preparation.
  • Can articulate the company vision, culture, sales processes.

Make sure you learn if this candidate is who you want while ensuring they have a great experience during the interview.

Onboard thoughtfully, don’t just throw information at new hires.

Great sales experiences are the result of thoughtful preparation.

Your training program should set new sellers up for success.

Ensure the new reps have a partner throughout their time ramping

No matter how impressive their sales career has been, this is a brand new role.

Set them up for success with a knowledgeable peer in place to help them overcome obstacles.

Teach your sales managers how to coach, manage, and lead

Through no fault of their own, most sales managers have not been given the skills to succeed.

A key to great sales experiences is a great front-line manager.

Support them with the right content

If you help them by making it easy to find the right content when they need it, they can focus their energy on selling, and that’s what they want to be doing.

Keep the rules of the game consistent

Stop changing the quota program every quarter.

Simplify data capture

Along the lines of the right content.

Do you know how to deliver horrible sales experiences?

Have sellers spend 25%+ of their week updating your CRM instead of focusing on sales activities.

When it’s not working, fix it or move on

The reality is, not every salesperson is going to be a good fit for your business.

The most successful sales teams don’t bank on previous sales experience to determine who will make it.

The best sales leaders will partner with Enablement to correct problems early, where possible.

These leaders will consider alternative roles in the business if it’s simply a skills mismatch.

And, the best leaders will be transparent when it’s not working and let the person move onto a new company where everyone has a better chance for success.

The bottom line is sales are not for everyone. However, if you want those with the right stuff to succeed, you cannot afford to leave sales experiences to chance.