A different view on interviewing sales people

A different view on interviewing sales people


Recruiting by pattern matching leads to a lot of churn, especially in startups. "Gee, she was a Senior Account Exec and hit 130% of quota at <Google, Microsoft, et al.> so she should hit 100% here at our startup with only 3 customers, no models of business value delivered, no local presales person, a website that we know isn't good,......"


Having sat on both sides of the table, behavioral based questioning ** around a current sales challenge or opportunity ** seems the most fair, and the most objective.


Flip the classic script of interrogation and hypothetical stuff to see how the person will interact with YOU, at YOUR company, with YOUR team, in YOUR market.


As a discussion around recent, real sales situation(s). Let the sales exec ask questions, discuss goals & potential challenges, how s/he would orchestrate the process, whom s/he would want to help, questions s/he will ask, how s/he will qualify.


Then role play with different stakeholders on your side (business head, users, IT people, internal support at the customer, etc.) and see how s/he responds, guides, executes.


This shows how s/he approaches a challenge, leverages strengths, thinks on the fly.


Shows the sales candidate how YOU handle questions, listen, problem solve together, and what it will feel like to work with you.


"Tell me about a time when you lost a sale..." questions are handled well by any decent sales person, can't be verified without violating privacy and NDAs.


"Past performance is no guarantee of future returns." Context matters.

Sales isn't sales.

Sales isn't sales.


Sales is helping prospects see value, see what's possible, see the future state of where they can be, and a way to get there.


Communicated by engaging, showing, informing.


Some practical tips.






Start with list of points to cover on one slide (2 if absolutely necessary) including demo highlights previously captured in discovery. And tweaked from your experience knowing the priorities of the audience. A simple list, not a slick "presentation" slide with logo and all. Not salesy.


If people interject, or suggest another point, then engage and see if others agree.


Look around the room for non-visual reactions. Gently ask if someone looks skeptical. Avoid going around the room asking, this slows things down while people are evaluating you, your offering, your company, and possibly thinking about other things. You can lose credibility quickly. Hesitation, long pauses, too many questions are interpreted as low competence --> lower confidence in you.


Use short and long pauses. This is an art, and elicits powerful responses.






Show a simplified block diagram only if absolutely necessary, such as showing distribution of the prospect's data to their clients if that's a "thing" for this audience. If they can grokk your value without a diagram, skip it. Less is more.


First demo as a "day in the life" from different perspectives (dashboards for execs, status for ops, metrics for marketing).


Target for a 3 minute demo. Rehearse with your team until you can do this faultlessly.


So if senior people have to leave, they have seen the VALUE of your offering. They will engage further, ask you to show others, etc.


Earns confidence through competence.





If your demo is good, you WILL get questions, reactions, skepticism, challenges. That's GREAT!


Get confirmation, ask for feedback, ensure you are meeting expectations. Display a list of points raised on a laptop as a live document in front of everyone. At this point, you're responding to the prospect, engaging visually, partnering...and doing this with the GROUP -- completely different from engaging 1:1 with stakeholders. Who is an influencer? Who is a skeptic? Who likes this? Who doesn't? Who has fears? Who may be a champion?


The AE has setup the meeting knowing who will attend, their concerns and roles. So you'll be ready to do deep-dives, or breadth-first responses across multiple perspectives, on-the-fly.


From this point, you can gauge what to prioritize, what to do next. A more detailed architecture. A longer demo showing more value, a version showing "how" dashboards are created, performance metrics, etc.

Customer success in enterprise sales

When should customer success become part of an enterprise sales process?


The earlier the better. Certainly after the key decision-makers and users are positive.


Startups stumble in the sales process to define value and impact for the customer.


In other words, what success looks like post-sale.


Generally because customer success (CS) is not engaged soon enough.


As stakeholders are positive, CS should be part of the team, define business and user milestones, with dates based on similar prior experience, and...


metrics of success



All users should be onboarded by <date>.

ADU (average daily usage) should be 1 hour one month after go-live.

ADU should increase to 3 hours per user per day 2 months after go-live, contingent on...

feature x delivered by that date

completion of training AI models at 98% accuracy or better

false positive rate of y% or less

average latency on user response to function z no greater than 900ms

explanations from AI acceptable to users



These metrics can be prepared by CS, with support from pre-sales, and reviewed by sales.


And openly discussed through the sales process.


Post go-live is a critical period when satisfaction can drop off quickly, usage drops off if users are confused, it's easier to go back to the old way, etc.


CS followup then becomes "is the client achieving x, y & z per the plan"? Not "just checking in, we haven't heard from you for 2 weeks, hope everything is ok."


It also helps the seller team be ahead of the curve. If a milestone will slip, then CS can adjust the rest of the plan, look at ways to de-risk further slippage, and proactively notify the buyer. That way, the seller team is openly highlighting an issue, AND bringing a solution in the form of a revised plan. What does the buyer team need to do? By what dates? What other things might go wrong and what can we both do to mitigate that risk?


Communications is so important in de-risking delivery and the relationship.

Sales is like chess

In enterprise deals, for repeatable use cases, I have templates of action plans (= just the prospect/seller interactions from an account plan).


From "hello" to "thank you" to "next steps after initial delivery" etc.


As a full plan, and also organized by buyer role (users, execs, compliance, security, etc.) with milestones, dates, dependencies (what we the sellers do, what you the prospect does).


I tweak the template into version 1.0 for a specific client, specific use case, after initial discovery.


And maintain it as an ongoing doc, along with presales, CS, etc.


Send in advance to each stakeholder, then sit individually with each stakeholder group and go through this, literally side-by-side, on paper. Let the stakeholder question, challenge, probe, on why, when, alternative actions. Let him/her write on the plan, circle.


We're literally "on the same side," the f2f aspects are amazing (it's easy to sense concern, hesitation without asking annoying questions constantly).


Providing value through the sales process

Providing value through the sales process


Especially for startups, where establishing credibility comes in small steps that build momentum to larger steps.


Earn confidence through competence.



Every email, presentation, action, document, response, should exceed expectations in the buyer's mind.


Each time, every time, all the time.


Across the sales team (AE, presales, CS, tech team, architecture documents, proposals).


The enterprise AE is an IC on his/her part, AND also Q/A across all these elements (at least in a startup!).



Break tasks into subtasks, discuss the goal for each subtask, and put DATES to each subtask. 

Plan the work.

Work the plan.


The AE works with teammates to define dates on intermediate checkpoints.



Eric in Engineering will produce a latency test plan, with 3 scenarios, in 10 days.


As the AE discusses this with Eric, they might agree on:


Day after tomorrow, Eric shares draft 1.0 of the plan with the AE, presales, etc. This de-risks by making sure everyone is on the same wavelength.


3 days later, Eric shares test results on the first scenario. The AE can see how the data are presented, the presales can give insight on how close this is to what the prospect needs, VP Engineering may have insights, etc.


Scenario 1 is revised as necessary.


2 days later, Eric shares revised test results on scenario 1, and results for scenario 2. This ensures consistency in testing, and presentation of the results.


2 days before due-date, Eric shares the "final" results and documentation. This gives him time to revise.