Recruiting Challenges

Hiring has probably been the most humbling part of my journey as a founder. No playbook really prepares you for it. You hire with conviction, sometimes you get it right… and sometimes you learn the hard way. I do think we’re far better at it now and still learning every day. Over time, a few lessons have stayed with me: 1. Attitude first Early on, I would get impressed by strong resumes and polished interviews. But I’ve learned that mindset, ownership, and intent matter far more than skill. Skills can be built. Attitude rarely changes. 2. Trust, but verify This was a tough one. We didn’t do background checks initially and paid the price for it. From fake salary slips to inflated roles, it happens more often than we think. Now, background verification is a must. 3. Interviews aren’t enough Some of our biggest hiring misses looked perfect in conversations. A simple technical or practical test has helped us avoid surprises later. 4. Clarity is the founder’s responsibility If KRAs and KPIs aren’t clearly defined before hiring, the fault is ours not the candidate’s. Ambiguity at the start always shows up as misalignment later. 5. Hire differently as you scale In the early days, we leaned towards hiring and training from scratch. But as the company grows, the time and bandwidth to train reduces. Sometimes, it’s better to hire people who are already trained and can plug in faster. Hiring doesn’t get easy, it just gets more intentional. What’s one hiring lesson you’ve learned the hard way?

Lessons learned as we scaled hiring at Dropbox from 25 -> 1500 employees:  - Recruiting is all about timing, build relationships over time.    - Hiring is a team sport & recruiting is everyone’s job.    - Closing is more effective when you get more people involved: we introduced “eng closers”, who were highly resonant with technical talent.    - New grads will get pressure from their parents to join big companies – win parents over too.    - Make sure referrals don’t go into a black hole or people won’t want to submit referrals anymore.    - Get your ERGs involved. Offer up a social chat w. any candidate interested in ERGs.    - It can take several years to crack a new campus, so be patient. It pays off big eventually.    - Build your sourcing muscle early and start investing in your talent brand bc at some point you won’t be able to hire via inbound + referrals alone.   Recruiters, hiring managers, TA leaders, who have been through hypergrowth, what are some of your hiring learnings from being in the trenches?

Four months after joining, the senior executive I championed to hire told me, "I'm sorry, but I think I'm in over my head here.' Those words still echo in my mind. Some of my most memorable leadership lessons have come from hiring mistakes, and 3 stories in particular changed how I approach executive recruiting. Mark seemed perfect for heading our high-growth business unit. "𝘈𝘮𝘣𝘪𝘵𝘪𝘰𝘶𝘴, 𝘪𝘯𝘯𝘰𝘷𝘢𝘵𝘪𝘷𝘦, 𝘢𝘳𝘵𝘪𝘤𝘶𝘭𝘢𝘵𝘦" - these words appeared in everyone's feedback. His approach to driving business growth while taking people along impressed us. But, quickly, we smelt trouble: no concrete business plan, poor execution, and a growing list of excuses. "𝘐'𝘷𝘦 𝘢𝘭𝘸𝘢𝘺𝘴 𝘸𝘰𝘳𝘬𝘦𝘥 𝘸𝘪𝘵𝘩 𝘭𝘢𝘳𝘨𝘦 𝘵𝘦𝘢𝘮𝘴 & 𝘦𝘴𝘵𝘢𝘣𝘭𝘪𝘴𝘩𝘦𝘥 𝘱𝘳𝘰𝘤𝘦𝘴𝘴𝘦𝘴," he finally admitted. "𝘛𝘩𝘪𝘴 𝘴𝘵𝘢𝘳𝘵𝘶𝘱 𝘦𝘯𝘷𝘪𝘳𝘰𝘯𝘮𝘦𝘯𝘵 𝘪𝘴 𝘤𝘰𝘮𝘱𝘭𝘦𝘵𝘦𝘭𝘺 𝘢𝘭𝘪𝘦𝘯 𝘵𝘰 𝘮𝘦." 𝗖𝗼𝗻𝘁𝗲𝘅𝘁, 𝗜 𝗹𝗲𝗮𝗿𝗻𝗲𝗱, 𝗶𝘀𝗻'𝘁 𝗷𝘂𝘀𝘁 𝗶𝗺𝗽𝗼𝗿𝘁𝗮𝗻𝘁 - 𝗶𝘁'𝘀 𝗲𝘃𝗲𝗿𝘆𝘁𝗵𝗶𝗻𝗴. Then there was Ron, interviewing for a sales leadership role. In our first conversation, he was eloquent about thought partnership being the true measure of client centricity. He even shared a touching ritual he'd created to help his teams combat the loneliness of sales work. I was ready to hire him on the spot. The second conversation felt like meeting a different person. "𝘊𝘰𝘭𝘭𝘢𝘣𝘰𝘳𝘢𝘵𝘪𝘰𝘯 𝘪𝘴 𝘧𝘰𝘳 𝘴𝘰𝘧𝘵𝘪𝘦𝘴," he declared. "𝘖𝘯𝘦 𝘴𝘵𝘳𝘪𝘬𝘦 𝘢𝘯𝘥 𝘺𝘰𝘶'𝘳𝘦 𝘰𝘶𝘵 - 𝘵𝘩𝘢𝘵'𝘴 𝘮𝘺 𝘱𝘰𝘭𝘪𝘤𝘺." When I asked if he'd apply that standard to himself, his response: "𝘕𝘰, 𝘵𝘩𝘦 𝘳𝘶𝘭𝘦𝘴 𝘢𝘳𝘦 𝘥𝘪𝘧𝘧𝘦𝘳𝘦𝘯𝘵 𝘶𝘱 𝘩𝘦𝘳𝘦. 𝘐𝘵'𝘴 𝘯𝘰𝘵 𝘧𝘢𝘪𝘳, 𝘣𝘶𝘵 𝘯𝘦𝘪𝘵𝘩𝘦𝘳 𝘪𝘴 𝘭𝘪𝘧𝘦." 𝗦𝗼𝗺𝗲𝘁𝗶𝗺𝗲𝘀, 𝘁𝗵𝗲 𝘀𝗲𝗰𝗼𝗻𝗱 𝗰𝗼𝗻𝘃𝗲𝗿𝘀𝗮𝘁𝗶𝗼𝗻 𝗿𝗲𝘃𝗲𝗮𝗹𝘀 𝘁𝗵𝗲 𝗽𝗲𝗿𝘀𝗼𝗻 𝗯𝗲𝗵𝗶𝗻𝗱 𝘁𝗵𝗲 𝗽𝗼𝗹𝗶𝘀𝗵. The most profound lesson came from Ritika. Her first interview was disappointing - nervous & fumbling. Something made me pause and we met face-to-face in our offices. A different person emerged. She later told me that being in the physical space helped her envision herself in the role and let her authentic self shine through. 𝗧𝗼𝗱𝗮𝘆, 𝘀𝗵𝗲 𝗵𝗮𝘀 𝗮 𝘁𝗵𝗿𝗶𝘃𝗶𝗻𝗴 𝗰𝗮𝗿𝗲𝗲𝗿. These experiences taught me three fundamental truths about senior hiring: First, real discovery happens in the second conversation, when guards come down and authentic personalities emerge. Second, success is deeply contextual—what works in a Fortune 500 might fail in a startup. That's why I create immersive 'day in our life' experiences. Finally, some of our best leaders may initially seem like rough diamonds; they just need the right environment to shine. 𝗔𝘀 𝗹𝗲𝗮𝗱𝗲𝗿𝘀, 𝗼𝘂𝗿 𝗷𝗼𝗯 𝗶𝘀𝗻'𝘁 𝘁𝗼 𝗱𝗲𝗹𝗲𝗴𝗮𝘁𝗲 𝗿𝗲𝗰𝗿𝘂𝗶𝘁𝗶𝗻𝗴 𝗯𝘂𝘁 𝘁𝗼 𝗼𝘄𝗻 𝗶𝘁, 𝗹𝗼𝗼𝗸𝗶𝗻𝗴 𝗯𝗲𝘆𝗼𝗻𝗱 𝗽𝗼𝗹𝗶𝘀𝗵𝗲𝗱 𝗿𝗲𝘀𝘂𝗺𝗲𝘀 to find those whose values and adaptability align with our context. #Leadership #Hiring

In IT recruiting, I’ve seen this more times than I can count. A hiring manager says: ❌ “The candidate rate is too high.” ❌ “We already have this profile from different vendor.” ❌ “No feedback. or Sudden New Update” ❌ “We’ll keep the resume for different role .” Many recruiters stop there. They see the rejection… and move on. But the real opportunity? It’s beneath the surface. Instead of negotiating blindly or just “checking back later,” change the approach: ✔ Ask what skill gaps the current team is struggling with ✔ Understand the business impact of the role staying open ✔ Identify what the current vendor isn’t delivering ✔ Reframe the conversation from rate to ROI (time-to-fill, quality, retention, project delay cost) Now let’s talk about the other side — candidate challenges. Because sometimes the issue isn’t budget. It’s market reality. In today’s IT hiring market: ❌ Niche tech stacks have a limited talent pool ❌ Strong candidates have 3–4 offers in hand ❌ Candidates reject onsite/hybrid roles ❌ Visa constraints shrink the available pool ❌ Long interview cycles cause offer drop-offs ❌ Unrealistic rate vs. skill expectations create mismatch If we don’t address these realities upfront, we waste weeks sourcing profiles that won’t convert. So instead of just “finding candidates,” shift the conversation: ✔ Calibrate must-have vs. good-to-have skills ✔ Align budget with market rates ✔ Shorten interview turnaround ✔ Sell the opportunity, not just screen resumes ✔ Position the role competitively against other offers Same goal: closing the position. Different approach: solving the hiring challenge on both sides. In IT recruiting, the real value isn’t in sending 10 resumes. It’s in aligning business expectations with market reality. Dig deeper. That’s where the real placements happen. 🚀 #ITRecruiting #TechRecruiter #TalentAcquisition #StaffingLife #HiringChallenges #RecruitmentStrategy

🟣 Reflections on Hiring Creative Talent I continue to spend a lot of time thinking about hiring in the creative world. The reason is simple: it’s where most of my time currently goes. Unlike many other functions, there isn’t a clear playbook for hiring creative talent in a scale-up environment, so in many ways I feel like we’re writing that playbook one chapter at a time. Almost every week, I sit down with my HR business partner to reflect on what we’re seeing in the market. Together, we’ve probably screened more than 200 candidates so far. I also regularly compare notes with Nithin Kuriakose , who is hiring in the design and UX space, and those conversations have been incredibly helpful. A few lessons stood out to me this week. 1) First, what a “good profile” looks like in a scale-up is very different from what it looks like in a large corporate environment, which is where I first learned how organizations hire. In a scale-up, we are often looking for zero-to-one or one-to-ten builders—people who know how to create something from the ground up. That is fundamentally different from operating within a well-established system. For example, someone may have done exceptional PR work or led major campaigns in a large organization. But doing that within a mature system with clear processes, large teams, and defined structures is very different from building those capabilities from scratch in a fast-moving environment. 2) Second, many candidates coming from corporate environments understandably approach problems from a “this is how we used to do it” mindset. While that experience can be valuable, it doesn’t always translate well to a scale-up where processes are still evolving and adaptability is critical. Because of this, I’ve found that the most effective part of our hiring process is the case study We give candidates a real scenario from our world, something a fintech scale-up like Tamara might actually face and ask them to work on it over the course of a week. This approach does two important things: • It gives us a clear window into how the candidate thinks and approaches problems. • It also gives candidates a realistic sense of what working in a scale-up looks like: a place where you are expected to build, experiment, and often wear multiple hats, rather than step into a fully developed system. In many ways, the case study becomes the closest simulation of the job itself. How do you approach hiring?

When a search drags past 60 days — I take full ownership. I just closed a six-month aerospace search that should’ve wrapped in half the time. No urgency. No internal champion. No pain. Comp bands straight out of 2019. I took it anyway. Because this is where the truth shows up — in Aerospace & Defense, it’s rarely “we just haven’t found the right person.” You have the right people. They just don’t believe the story. Every A-player in this market runs the same checklist before saying yes: • Mission clarity – Do they know where they’re going? • Decision velocity – Can this team actually move? • Leadership consistency – Who will I really be working for? If your interview panel can’t tell the same story about the role — your pipeline isn’t broken. Your message is. Great aerospace talent isn’t turned off by complexity. They’re turned off by ambiguity. #AerospaceRecruiting #DefenseTalent #HiringStrategy #ExecutiveSearch #LeadershipAlignment #MissionCriticalTalent #GovCon

Had a call last week with a GovCon CEO who told me something that stuck with me: "Casey, we've been trying to fill this TS/SCI with poly role for 7 months. We've worked with two recruiters. Posted everywhere. Nothing. I'm starting to think the talent doesn't exist." I asked him to send me the job description. Within 2 minutes, I found the problem. They were asking for 10+ years of experience, three specific certifications, active TS/SCI with poly clearance, AND they wanted someone local to Northern Virginia willing to work on-site 5 days a week for below-market salary. The issue wasn't that the talent didn't exist. The issue was that they were looking for a unicorn and offering horse pay. Here's what nobody tells small GovCon companies: You can't compete with the major defense contractors on every dimension. So you need to pick your battles. Can't match their salary? Lead with mission impact and career growth. Can't offer full remote? Highlight the meaningful work and team culture. Need very specific experience? Be willing to train on some of the "nice to haves." Cleared talent is scarce. But unrealistic expectations make it impossible. Sometimes the problem isn't the market. It's the requirements.

Can you just explain it in plain English? The hiring manager's frustration was obvious during my client's interview. Despite 15 years leading intelligence operations, this Senior Chief couldn't get civilian employers to understand his value. The problem wasn't his experience. It was his language. Military skill translation is the second-highest challenge facing transitioning warriors according to my recent poll. Here's why it matters more than most realize... 🔸 Recruiters spend 6 seconds scanning your resume 🔸 ATS systems filter out military terminology they don't recognize 🔸 Hiring managers can't advocate for candidates they don't understand 🔸 Your accomplishments become invisible when wrapped in acronyms But here's what most resume services get wrong about translation. They focus on the WHAT. They ignore the WHY and the IMPACT. Let me show you the difference. Military Language: "Served as Battalion S4, managing $8M in equipment accountability and coordinating logistics support for 600-person organization." Translated But Still Weak: "Managed supply chain operations and equipment inventory for large organization." Strategic Translation That Gets Interviews: "Directed supply chain operations ensuring 100% equipment availability across 600-person organization, implementing inventory tracking system that reduced loss by 40% and saved $250K annually." See the difference? The third version answers the questions every hiring manager is asking: 🔸 What specific problem did you solve? 🔸 How did you measure success? 🔸 What was the business impact? 🔸 How does this apply to MY organization's challenges? I worked with that Senior Chief for two weeks on strategic translation. We identified that his intelligence operations experience wasn't about "gathering information." It was about "risk analysis, pattern recognition, and data-driven decision making under uncertainty." Suddenly, his military background became relevant for corporate security, business intelligence, and strategic planning roles. He landed three final interviews within 30 days. (Yes, all from referrals... don't stop networking now...) 🔸Your mission planning becomes project management. 🔸Your equipment accountability becomes asset optimization. 🔸Your team leadership becomes change management and talent development. The translation isn't about dumbing down your experience. It's about amplifying your impact in terms that create immediate recognition. What military skill are you struggling to translate for civilian employers? If you're on the struggle bus and want some support, DM me... I'd be happy to hop on a call or connect you with one of my fellow career coaches.

Every manager knows that moment... Staring at an inbox full of resumes. Wondering if the perfect candidate is hiding somewhere in there. The pressure can be overwhelming. I know—I've been there. Here are 12 powerful lessons I've learned  about recruiting top talent: 1) Don't list generic tasks and outdated requirements. ↳ Top performers want to see the impact they'll make,  not just task lists. 2) Don't skip explaining the "why" behind the role. ↳ A-players want to be part of something meaningful. ↳ If you can't articulate your "why,"  you'll lose them before you begin. 3) Don't just post and pray for the perfect candidate. ↳ You need to actively hunt through networks  and build meaningful connections. 4) Don't hire based purely on "likability." ↳ Look for people who'll challenge your thinking  and bring fresh perspectives. 5) Don't create a maze of repetitive rounds. ↳ Keep it focused and respectful of candidates' time. 6) Don't assume money alone attracts top talent. ↳ Offer more than a competitive pay. ↳ A-players want to know how they'll grow and learn. 7) Don't rely solely on past experience. ↳ Give candidates real problems to solve. ↳ Their approach tells you more than their  resume ever will. 8) Don't leave candidates hanging. ↳ Ghost a candidate, and you've lost them forever. ↳ Regular updates show respect and build trust. 9) Don't make decisions in isolation. ↳ Include your best people in the hiring process. ↳ They'll spot things you might miss. 10) Don't hire just to fill an immediate need. ↳ Look for people who can grow into tomorrow's  challenges. 11) Don't ignore your online presence. ↳ Top talent researches you thoroughly. ↳ What story are you telling online? 12) Don't overwhelm new hires with information. ↳ A smooth onboarding shows you've got  your act together. Some days, it’ll feel impossible to find the perfect fit. But remember: you're not just filling a role. You're building your company's future. The right person is worth the search. ♻️ Find this helpful? Repost for your network. 📌 Follow Amy Gibson for practical leadership tips.

Transitioning from the uniform to the boardroom is less about "starting over" and more about "re-translating" a lifetime of expertise. I recently had a conversation with a military officer preparing for this move, and it struck me that while the landscape changes, the fundamental requirements for leadership remain constant- they just require a different lens. Here are three core insights I shared from my own transition (please feel free to challenge or add to them): 1. Master the Art of the Interlocutor In the private sector (especially if you remain the the defence industry), your greatest value is often acting as the bridge between fellow senior executives and those unfamiliar with the defence ecosystem. Whether you are translating your own military skills into business value or explaining defence imperatives to engineers who are building the next generation of solutions, you must be a dual-linguist. The Goal: Deeply understand (and be ready to explain) your trade, how the business of government and defence operates, and how the technology functions in that environment before you step out of the door. If you cannot communicate the "why" to both a CEO and a developer, the mission fails. 2. Embrace the Numbers Public service and military life rarely demand the same level of financial acuity required in industry. Private organisations cannot survive without leaders who embrace data. Transparency, manageability, and market reporting are the lifeblood of the private sector. The Shift: Get comfortable with the balance sheet and the revenue pipeline. Managing by the numbers is not just an administrative task; it is the primary way industry leaders navigate and prove success. 3. Challenge the "Command and Control" Myth There is a persistent Hollywood-fuelled stereotype that military leaders only thrive in rigid, "do-as-I-say" environments. In reality, large private sector corporations are often just as hierarchical as any military organisation-they simply use different cultural symbology. And they can be just as bureaucratic. (If you are yearning to break free consider embracing entrepreneurism instead). The Opportunity: Do not let the stereotype define you. Be ready to demonstrate how military principles like Mission Command and Mission-Orientation make you more flexible and resilient than your peers. Your ability to operate in the "grey" and deliver results amidst ambiguity is a superpower in any commercial setting. To those currently in the process of hanging up the uniform: the bridge to industry is built on your ability to translate your past excellence into their future growth. #MilitaryTransition #Leadership #DefenceIndustry #VeteranHiring #CareerChange