As a business owner and entrepreneur one of the best skills you can have is finding the right people, for the right task or job in your company.
When it comes to looking for sales growth help outside of your company it is important to know: Who should I hire as an independent rep (IR) and what should I look for?
Full disclosure, I’ve been a business owner for over 20 years, in B2B sales for over 30 years and an independent B2B representative for 15 years and it is with this point of view I offer this advice on these 3 key points:
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Make sure the personal chemistry is right
This may seem like an item that should be way, down the list considering there are so many other important factors to consider, like: knowledge of my industry or sales experience overall and how organized are they, but this is my list and from my perspective the most important. Why you ask?
In my experience a team that is on the same wavelength and are naturally compatible with achieve greater results short and long term than one that does not. Think of it this way, effective teamwork and a harmonious working culture will be a more enjoyable journey and lends itself to problems solving as opposed to problem creation through clashes.
In this don’t look for clones of yourself or your style. Actually, embrace the differences and look for people that have strengths to your weaknesses that are professional, open-minded and still have the ability to learn new things.
Questions to ask to measure potential chemistry:
Personal and Professional Values Alignment
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What motivates you to succeed as an independent sales representative?
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How do you define integrity in a business relationship?
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What values are most important to you in your work, and how do they show up in your interactions with clients and partners?
Communication and Collaboration Style
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How do you typically communicate with clients and team members—do you prefer calls, emails, or face-to-face meetings?
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How do you handle disagreements or misunderstandings in a business relationship? Can you share an example?
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What type of feedback do you find most helpful, and how do you prefer to receive it?
Work Ethic and Accountability
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Can you describe how you manage your time and prioritize your workload?
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How do you keep yourself accountable for meeting goals and deadlines?
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Can you share a specific instance where you went above and beyond to close a sale or help a client?
Cultural Fit and Adaptability
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How do you approach learning about and adapting to a new company’s culture, products, and sales processes?
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What kind of company culture helps you thrive, and how do you contribute to it?
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Tell me about a time you had to adapt quickly to a change in strategy or goals—how did you handle it?
Vision and Long-Term Goals
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What are your long-term goals as an independent sales rep, and how does working with our company align with them?
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Where do you see this partnership in 1–3 years, and what would success look like for you?
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What are your expectations from this relationship, both personally and professionally?
Closing thoughts on chemistry
You’ll be able to tell a lot about what the chemistry may be like when you work with an IR by asking them all the questions. At the end of the day you may choose to ask them only a few or no questions related this area. It’s important you stay true to who you are as a business owner and your expectations of what you want as this may not be as important to you as it is to others.
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Verifiable B2B industry experience and skills with references
In this modern world, information is plentiful and knowledge, wisdom and personal connection are scarce. Unfortunately, it is quite easy (and getting easier with AI) these days for anyone to exaggerate or even outright lie about their business or personal experience and expertise.
Where the rubber always meets the road for me (and I’ve hired many independent contractors for sales and non-sales roles) is; “do then have references I can contact to verify whatever they have told me, if I choose?”
Direct Request for References
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“We’re really interested in learning more about your past successes. Would you be able to share a few references—clients, past employers, or partners—who can speak to your performance and professionalism?”
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“Could you provide 2–3 references who can confirm your sales achievements and share insights about what it’s like to work with you?”
Specific Verification Questions
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“We’d love to hear more about your experience. Could you connect us with someone who can verify the results you’ve shared and give us more details about the types of clients or industries you’ve worked with?”
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“To help us better understand your sales style and approach, could you share contact information for someone who can speak to your ability to generate leads and close deals?”
Reassurance for Transparency
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“We want to make sure this is a great fit for both of us. Could you share a couple of references we could speak with to get a better feel for your sales process and work ethic?”
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“It’s part of our process to talk with a few references to validate the experience we’ve discussed. Would you be comfortable sharing a few contacts we could reach out to?”
If They Seem Hesitant
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“I completely understand if some clients or past employers prefer privacy, but even general references, like someone you’ve partnered with on a project or a manager from a previous role, would be very helpful.”
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“If formal references are a challenge, perhaps a professional colleague or a long-term client could share insights about their experience working with you?”
Closing thoughts on verifying industry experience and skills
The “if I chose” part is a very important option for me, because it’s an option I’d like to have depending on how the rest of our initial meeting goes. It is also education to see someone’s reaction when you ask for people to talk to, it can tell you a lot about them and how they view their clients and business relationships, which if you work with them, you will be a part of. When asking these questions keep your tone professional, respectful, and non-confrontational, emphasizing that this request is a standard part of your approval process.
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How does your prospective IR deal with challenges and overcoming potential or realized failures?
It is important and useful to find out how anyone you will be working with deals this challenges and failures. If you read the biographies of many famous people the spectrum can be all over the place as failure in the corporate world is “often not and option” and a “taboo” subject, yet it will come along all the same, in a small or big way, pretty much everyday.
I’m the type who is curious about how people handle this subject from the point of view of being able to talk about it in an open or closed manner and also how they explain how they overcame the challenges in front of them.
Questions to ask on overcoming challenges and failures
General Approach to Challenges
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“Can you share a specific example of a significant challenge you faced in a sales role? How did you approach it, and what was the outcome?”
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“Tell me about a time when a deal you were counting on didn’t go through. What did you learn from that experience, and how did you adjust your strategy moving forward?”
Handling Rejection and Failure
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“Sales often involves rejection. Can you describe a time when you faced repeated rejections? How did you stay motivated and keep pushing forward?”
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“Have you ever had a client relationship fall apart? How did you handle it, and what steps did you take to rebuild trust or move on?”
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“Tell me about a time when you didn’t meet your sales quota or expectations. What actions did you take to turn things around?”
Problem-Solving and Adaptability
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“Can you share an example of a time you faced resistance or skepticism from a potential client? How did you win them over?”
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“Describe a situation where a deal or project didn’t go as planned. How did you pivot and salvage the situation?”
Reflection and Lessons Learned
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“What’s the biggest sales-related failure you’ve experienced? Looking back, what would you do differently?”
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“How do you typically process setbacks? Can you share a time when you used a failure as a stepping stone to improve your approach?”
Demonstrating Resilience
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“Sales can be unpredictable. How do you stay focused and motivated during periods of uncertainty or underperformance?”
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“Can you describe a time when external factors—like a market downturn or internal changes—impacted your ability to sell? How did you manage the situation?”
Closing thoughts on overcoming challenges and failures.
Before you introduce this line of questioning into a your process you should take stock of what you will be prepared to share regarding how you overcame challenges and failures and how you plan to approach the challenge you are asking your independent representative to solve?
Ask yourself how open-minded are you to be vunerable and share something uncomfortable, as you are asking the IR to do? Are you ready to change something in your sales process and if necessary company?
As an IR its amazing how many times I meet business leaders who are looking for solutions to their sales and business growth challenges as long as they don’t really have to make any changes to to their company, staff or industry norms. The people who I personally work best with are those that are open to implementing (not just listening to) my recommendations and are prepared to be disruptive in their industry and current standard sales and business practices.
How much leeway does your potential IR have to potentially try something new with you?
Wishing you success,
David Westdorp
David Westdorp Strategies
Direct: 778.994.3414
www.davidwestdorp.com