BL&T No. 127: Red Flags in Qualifying Employees & Clients

Agency Leadership

This post originally appeared in my newsletter, Borrowed, Learned, & Thought. BL&T is a weekly newsletter sent on Mondays. In every edition, I share weekly themes and progress in running an agency business/team and doing my best to live a good life. Published posts do not include all details shared via email to subscribers. Subscribe here.


"Most interview processes are deeply flawed. Some people interview well, and some people don’t. A person who doesn’t interview well may nonetheless be the best choice for the job. That’s why it’s so important to probe deeply, know what to listen for, and get supplemental data. It takes time and effort to drill down further, but it’s always worth the trouble."

From "Execution: The Discipline of Getting Things Done" by Larry Bossidy, Ram Charan, and Charles Burck [Book]


I was chatting with one of our Team Leads last week about red flags we see in interviews when hiring new folks. These are the sorts of warning signs that are hard to overlook, even if other characteristics of the candidate check out.

After our chat, I thought about the parallels between screening calls with prospective employees and initial calls with prospective clients. From qualification to engagement and retention, many aspects of the employee experience relate to the client experience. Just the other day, a prospect asked if we had any further questions during an initial new business call, remarking, "I know you're interviewing us just as much as we're interviewing you."

Over the years, we've experimented with various approaches to qualifying prospective employees and clients. The beauty of having these systems in place is they give you an objective way to say yes or no. At the same time, we've also learned (the hard way) it's often best to trust your gut. Doing so is especially difficult if the employee has an impressive pedigree or the client's profile fits your positioning like a glove. Add on the weight of staffing needs or a weak pipeline, and the pressure to say yes is that much worse!

Top 10

Last week, we decided to pass on two opportunities with new clients after initial calls. One was with a brand the team has admired for some time. Discussing our decision as a team reminded me of my conversation earlier in the week about hiring. So, I started jotting down some notes on the red flags I keep an eye out for when qualifying prospective employees and clients.

Below are my top 10 for each. I wouldn't call this list exhaustive, but I tried to cover a lot of ground. I didn't include common red flags like having an unachievable budget or salary request, being distracted, using foul language, appearing frazzled, or showing up late.


When I chat with prospective employees for the first time, I'm looking for someone who is growth-minded. They reflect on past challenges and take ownership of their decisions. They are curious and well-prepared. They want to know where we're headed as a company to see how they can contribute and collaborate.

Here are some red flags that point in the opposite direction:

  1. Citing the same issues in several past jobs, pointing fingers at their co-workers, managers, or the company
  2. Speaking at length about strengths but cannot cite any weaknesses or desired growth areas
  3. Speaking at length about achievements but is unable to share challenging experiences or past mistakes
  4. Speaking ill of past co-workers, managers, or companies as a whole
  5. Talking in broad strokes about their past roles, unwilling to get specific even when prompted with additional questions
  6. Using buzzwords or jargon to sidestep questions about their experience
  7. Over-stating why they are a good fit for the role vs. asking more questions to gain a better understanding of what success looks like in the role
  8. Noting that they left a past job because it was "not the right fit" but cannot speak to any lessons learned or takeaways
  9. Listing all the reasons how the company can help them advance their career
  10. Giving a vague response to what excites them about the potential role


When I chat with a prospective client for the first time, I'm trying to gauge if they have a clear idea of their goals as a business. They know what's worked and hasn't worked in the past. They are realistic about the levers they can pull to achieve their objectives or are eager to discover them with a partner. They welcome questions about their brand background. They are upfront about what they value in collaboration but are open-minded to learning about alternate ways of working.

Here are some red flags that point in the opposite direction:

  1. Citing the same issues in several past agency relationships, pointing fingers at the agency without acknowledging their role in the engagements
  2. Speaking ill of their co-workers, boss, or company as a whole
  3. Speaking with more than a few agencies or partners about the potential project with no plans to create a shortlist as a next step
  4. Citing multiple "key" stakeholders with no clear path for decision-making
  5. Unwilling to share or unable to articulate challenges with their current agency (who they will be firing)
  6. Sharing the importance of hitting an aggressive timeline but being unable or unwilling to commit time and resources to the project
  7. Speaking to the pain points and challenges of working with their CEO, founder, or leadership
  8. Expressing fear of working with agencies, citing a situation where an agency wronged them or their personal experience at an agency
  9. Expecting that the project at hand will help them achieve their business goals by itself
  10. Over-stating the significance of creating a design that no one has ever seen but unable to articulate their ideas, even when shown references

In The End

I've been in situations where we've ignored these flags, and everything turned out fine. But more often than not, we look back and see that the writing was on the wall.

I'm not suggesting that any of these flags should result in an immediate no to an employee or client; however, they should be enough to prompt a discussion. It might mean having a follow-up call with the employee or client or even talking to folks they've collaborated with before.

In the end, if we choose to move forward, we'll know what we're signing up for and can go in with a plan for managing the potential flag, should it come up.

Related: Learning from Client and Employee Turnover

Thought Starter

What red flags matter most to me during qualifying calls with prospective clients and employees?


The E-Commerce Corner

Click here for the Twitter thread version of this list.

Last week, Shopify released 100+ product updates in their 2023 Winter Edition. Some of these are already available, while others are coming soon. There are a ton of exciting updates, but here are the 10 that caught my eye:

  1. Drag-and-drop checkout editor for more brand consistency, plus app integration for extended functionality: Clients often ask how we can make checkout feel more like an extension of their brand and website. These updates will be a game-changer for more turnkey customization and merchants looking for a more advanced robust cart/checkout experience.
  2. Shop Promise badge (on product pages) will display smart delivery dates backed by a limited guarantee: Maybe it's just me, but this feels like a response to Amazon's Buy with Prime value prop. Either way, I'm excited to see this in action and think it can be effective in building customer trust and confidence. Shopify claims up to 25% life in conversion.
  3. Deeper Shop Pay integration (one-click checkout & using passkeys for accounts): As a customer, I've loved the ease of Shop Pay. It's great to see Shopify embed it further into the customer journey. One-click checkout will make repeat purchases seamless. On the accounts side, we see more clients opting to go live without account pages, but leaving customers to rely on email alone can be tough. Making account creation and management easy with Shop Pay will be a value-add to merchants and customers alike. Great thread from Shopify Senior Product Lead, Patrick, here.
  4. AI-generated storefront content (Shopify Magic), e.g. use keywords to generate product descriptions: Copy is often a pain point for clients, so I'll be curious to see how effective/easy this is to use. I'm sure we'll see AI continue to show up more in all aspects of e-commerce.
  5. Improved search & recommendations: Smart, suggestive search has become the expected functionality for e-commerce stores with more than a handful of SKUs. It's nice to see Shopify's focus on Search and leveraging data across Shopify to improve it.
  6. Introducing Metaobjects, allowing merchants to create reusable, custom content: Like the drag-and-drop checkout editor, this feels like another step in the "no-code" direction. As an avid-Webflow user, I'm loving this update. I'm also looking forward to seeing how our designers can weigh in on what should be a metaobject, based on how they structure their design files.
  7. Product Bundles: Finally, the new Shopify Bundles app will make product bundling easy for merchants — a long-time request we've heard from clients.
  8. More Shop app customization (branding, shop experiences, etc): I don't hear many people talking about the Shop app; however, I think it can be a powerful tool for customers and merchants alike. It's interesting to see Shopify investing in new features. It makes me wonder if an Amazon-like experience is a long-term vision. I'll be eager to see if this drives adoption.
  9. Translate & adapt app, making it easy to localize store content across markets: We see this request a lot, especially for skincare and beauty clients with different laws/guidelines by region. This will be a powerful upgrade across the board.
  10. Integrated marketing automation for re-engagement with Shopify Email: I didn't expect to see Shopify prioritizing email, but so far, it looks like a solid offering for merchants who don't need or want to invest in a more robust email offering with Klaviyo.

Check out the Shopify 2023 Winter Edition page for the full list of updates, along with more details, documentation, and explainer videos.

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