10 Harsh Truths about Hiring an Executive in 2025
Everyone talks about hiring executives like it’s just finding a good “company guy” with a strong résumé. That’s fiction.
The actual truth? Even awesome companies screw it up, especially at early growth stages. You’ll hear polished lines in every board meeting, but no one tells you how often the wrong people land in critical positions.
This piece cuts through the noise. You’ll get brutal truths, pulled from experience, failure, and those painful postmortem calls.
If you care about company goals, team dynamics, or how to avoid turning your leadership team into a bad work experience, read on.
Why do great executives matter?
Here’s why it’s always going to be important to connect with the right executives for your company.
They scale the company beyond the founding team’s limitations. A startup might be built by builders, but hitting product-market fit and growing a real company requires operators who’ve seen the movie before.
They align the chaos. During the messy stages of growth, a strong executive team translates ambition into execution. Without them, you're just reacting.
They create lasting systems, not just temporary output. A great head of sales doesn’t just sell; they build systems, train others, and turn a team into a revenue machine.
They make you look competent to the outside world. Investors, acquirers, and potential hires use your leadership team as a proxy for long-term viability.
They act as beacons for talent. The right executive roles attract better candidates across the company. The wrong ones repel.
They protect the founding team from burnout. Without seasoned help, founders become overloaded and fall into reactive mode.
They bring truth into the room. With strong active listening skills and decision-making instincts, good execs challenge your blind spots instead of validating your bias.
They either increase or kill your chance of success. There are billions of people, but only a few who will move the needle. One great hire can make the company. One bad hire can stall it.
What are the biggest executive hiring challenges in 2025?
Let’s take a look at some of the biggest challenges facing companies when it comes to hiring executives in 2025.
Too many resumes, not enough relevance. Companies face a flood of candidates who look qualified but lack the specific combination of skills needed for their company goals, product, and stage.
Everyone’s hiring the same people. Top execs are constantly getting pinged. If your executive position isn’t differentiated, you’re not getting replies.
Mismatch between startup needs and big-company reflexes. A former VP from a company with hundreds of employees may flounder in a five-person startup without process or structure.
Compensation expectations are out of sync. Compensation at growth often includes equity and long-term upside, but many execs want upfront guarantees or cash-heavy deals.
The nonprofit trap. Some orgs, especially mission-driven ones, default to hiring people with strong nonprofit experience, which doesn't always map to startup execution speed or adaptability.
Search fatigue is real. A bad hire resets the timeline by 6–12 months. Multiple rounds of vetting, especially with a board search committee, can drag out decisions and wear everyone down.
Culture-fit clichés can hide real misalignment. Founders often default to hiring someone they’d grab a drink with, ignoring whether the exec can truly operate or lead.
Too much advice from people who aren’t hiring. Founders rely on investor input or advice from a16z posts and every blog post that sounds smart, rather than a real-world signal.
10 Harsh Truths about Hiring an Executive in 2025
1. Some of the best execs want to join a company, not build one from scratch
Many executives prefer to join established companies with existing systems and processes rather than build one from the ground up. In 2025, this preference seems to be growing, as executives seek roles where they can make use of their experience within structured environments.
Startups still in the early stages of forming a company from a product might find it challenging to attract this kind of talent. Executives may perceive these startups as "too early," even if they don't express this directly.
The graphic below highlights the choice top executives are facing here:
The executive hiring landscape in 2025 is marked by a preference for roles in companies that have achieved product-market fit and possess established operational frameworks. According to a report by Collingwood Search, executives with a coaching approach who prioritize empowerment, mentorship, and results are a great fit for companies that have moved beyond the initial startup phase. This shows the importance of having a clear company structure to attract top executive talent.
Also, the demand for executives who can drive sustainability strategies and lead initiatives aligning with global goals is on the rise. Companies are increasingly seeking leaders with experience in sustainable business practices, environmental stewardship, and social responsibility. These executives are more likely to join organizations where they can implement these strategies effectively, which typically requires an established company infrastructure.
Startups that want to attract top executive talent in 2025 need to recognize the importance of having established systems and a clear operational framework. Without these, they’ll struggle to convince experienced executives to join their ranks, as many prefer environments where they can apply their skills within a structured setting.
2. Being a “company guy” isn’t a compliment if your company is broken
The label "company guy" tends to refer to unwavering loyalty to an organization. While commitment is generally commendable, it's also important to discern when such loyalty leads to dysfunction. Executives who stay in toxic environments without challenging the status quo may inadvertently sustain mediocrity and hinder organizational growth.
A study by iHire revealed that 74.9% of employees have worked in toxic workplaces, with 78.7% attributing the toxicity to poor leadership or management. This shows the significant impact leadership has on workplace culture. What’s more, 53.7% of employees have quit their jobs due to negative work environments, which shows the tangible consequences of sustained dysfunction. The image below summarizes these findings.
On top of that, a report by Businessolver found that 52% of CEOs acknowledged their workplace culture as toxic, a notable increase from previous years. This admission from top leadership indicates a growing awareness of internal issues, but also raises concerns about the effectiveness of existing leadership when it comes to addressing and rectifying these problems.
While loyalty is a valued trait, it's essential for executives to pair it with the courage to challenge and improve broken systems. Organizations should hire leaders who demonstrate commitment but also possess the vision and fortitude to drive positive change.
3. A résumé filled with big titles means nothing without context.
In 2025, a résumé adorned with impressive titles like "Senior Vice President" or "Chief Strategy Officer" may not carry the weight it once did. The phenomenon of title inflation, where individuals hold grandiose titles without commensurate responsibilities or achievements, has become increasingly prevalent.
For instance, a Wall Street Journal report highlighted that companies like J.P. Morgan and Johnson & Johnson have roles labeled as "senior" that require as little as one to three years of experience. This kind of thing complicates the hiring process, as titles no longer reliably indicate a candidate's experience or capabilities.
Moreover, the rise of Applicant Tracking Systems (ATS) has shifted the focus from titles to quantifiable achievements and relevant keywords. Research suggests that 75% of résumés are rejected by ATS before reaching a human recruiter, primarily due to a lack of context or relevant content. This highlights the importance of providing concrete examples of impact, such as "increased sales by 30% over two quarters," rather than relying solely on lofty titles.
Hiring managers are now encouraged to go deeper into a candidate's actual contributions and the context of their previous roles. A title alone is no longer enough; understanding the scope of responsibilities, the challenges faced, and the tangible outcomes achieved provides a more accurate picture of a candidate and their suitability for a leadership position.
4. You may well hire the wrong person first
Hiring the wrong executive isn't just a misstep, it's a costly error that can significantly impact a company's trajectory. Even with a well-structured board search committee, the process is fraught with challenges. Studies indicate that executive failure rates within the first 18 months range from 30% to 50%. This high turnover shows the difficulty in identifying candidates who possess the requisite skills and also fit with the company's culture and vision.
The financial implications of a mis-hire are substantial. For instance, the cost of a failed CEO can range from $12 million to $50 million, considering factors like recruitment expenses, severance packages, and the ripple effects on company performance. These figures don't account for the intangible costs, such as diminished team morale and lost strategic opportunities.
Given these risks, companies need to approach executive hiring with a well-thought-out strategy. This includes in-depth vetting processes, realistic timelines, and contingency plans for potential mis-hires. The image below shows some more ways to avoid and mitigate mis-hires.
Recognizing that the first hire may not always be the right fit allows organizations to remain agile and responsive, which leads to long-term success despite initial setbacks.
5. A great interview can still hide a bad person
Executive candidates often excel at presenting themselves during interviews, showcasing polished communication and storytelling skills. However, these abilities can sometimes mask underlying issues that only surface once they're in the role. Research has found that up to 1 in 5 new employees leave a new role within the first 45 days, often due to poor fit, something thorough reference checks might have flagged.
To mitigate such risks, it's crucial to conduct thorough reference checks that go beyond surface-level inquiries. Engaging multiple references, including former supervisors and colleagues, can provide a more in-depth view of a candidate's past performance and behavior. The more the better: relying solely on one or two references can compromise the effectiveness of the process.
In the graphic below, you can see how to get better results through reference checks:
Incorporating structured reference check questions can improve this process. For instance, asking about specific instances where the candidate demonstrated leadership or handled conflict can reveal insights not apparent during interviews. These types of questions can uncover a candidate's leadership style, decision-making abilities, and cultural fit.
Ultimately, while interviews are essential, they shouldn't be the sole factor in executive hiring decisions. Comprehensive reference checks serve as a key tool to validate a candidate's suitability and help organizations make informed hiring choices.
6. Executives rarely scale across all growth stages
In 2025, it's increasingly evident that executives who excel in one phase of a company's growth may not thrive in another. A leader who is effective in a startup environment, characterized by rapid changes and minimal structure, might struggle in a more mature organization that requires formal processes and scalability. Conversely, an executive accustomed to the resources and systems of a large corporation may find it challenging to adapt to the resource constraints and ambiguity of an early-stage startup.
Check out the image below for a breakdown of these challenges:
Research underscores this mismatch. According to a study, 50% to 70% of executives fail within 18 months of taking on a new role, regardless of whether they were external hires or internal promotions. This high failure rate suggests that success in one organizational context doesn't guarantee success in another.
The implications are significant for hiring. Companies need to assess not only a candidate's past achievements but also their adaptability to the company's current stage and future trajectory. This means evaluating their experience with similar organizational sizes, cultures, and growth phases. By aligning executive capabilities with the company's specific needs, organizations can boost the likelihood of a successful leadership fit.
7. Some executives are politicians in operator clothing
Today’s corporate landscape is increasingly plagued by executives who excel at managing perceptions rather than delivering tangible results. These individuals often thrive in boardroom settings, articulating grand visions and strategies, yet fail to translate these into measurable outcomes. This phenomenon, sometimes referred to as "managing up," involves prioritizing relationships with superiors over effective team leadership and operational execution.
In the graphic below you can see the dangers of this kind of leader:
To mitigate these risks, organizations need to implement robust evaluation and feedback mechanisms. Regular 360-degree feedback, performance metrics aligned with strategic goals, and a culture that values transparency and accountability are essential.
Performance metrics aligned with strategic goals are also critical. Projects with clear performance measurement systems are twice as likely to be perceived as successful, but only 37% of projects actually establish success criteria early, implement guiding measurement systems, and track metrics throughout the project. This gap shows how important it is for organizations to prioritize structured measurement and accountability so that leadership effectiveness is grounded in tangible results, not just perception.
This way, companies can distinguish between leaders who genuinely drive progress and those who merely project the illusion of competence.
8. Executive hiring is where idealism gets expensive
In 2025, executive hiring remains a high-stakes endeavor where idealism can lead to costly missteps. While it's tempting to bet on a candidate's potential, overlooking proven performance can result in significant financial and organizational setbacks. The cost of a bad hire is high. For executive roles, this can translate into financial losses of $240,000 or more per mis-hire.
To mitigate these risks, companies should implement rigorous evaluation processes that prioritize tangible accomplishments and cultural fit. This includes comprehensive reference checks, performance-based assessments, and scenario-based interviews that reveal how candidates have navigated challenges similar to those they will face in the new role.
The funnel below shows what this process might look like:
By grounding hiring decisions in concrete evidence rather than idealistic expectations, organizations can enhance their chances of securing leaders who will drive sustainable success.
9. You might not know their actual impact until 6–12 months in
In 2025, one of the most common mistakes in executive hiring is expecting immediate results. Unlike entry-level roles where output is visible in days or weeks, executive impact often takes 6 to 12 months to become measurable. In fact, structured onboarding plans for executives can take up to 9 months, with meaningful contributions and clear success metrics generally emerging after this period, not before.
That’s because senior hires need time to assess team dynamics, diagnose internal systems, and influence cross-functional change. Part of the reason why so many executives fail within 18 months is that the early performance window was misread or the onboarding was rushed.
The image below shows how this process can play out:
This delayed clarity makes hiring risky. It’s why over-relying on first impressions: polished interviews, high-profile resumes, charismatic boardroom presence, can backfire. That’s why smart companies now test executives with consulting projects, paid trial periods, or scoped OKRs during the first quarter, before handing over full ownership. It’s not about distrust. It’s about protecting team momentum, equity, and morale.
10. Hiring execs without a clear strategy is like building a sports team without positions
Hiring executives without a clear strategy is akin to assembling a sports team without assigning positions. In 2025, many startups fall into the trap of recruiting based on general talent or impressive resumes and fail to define specific roles and responsibilities.
This approach often leads to confused expectations and underutilized skills, and results in stagnation rather than progress. For instance, bringing on a seasoned sales leader without a clear mandate, such as "fix revenue operations" or "bridge Technical to Product to Sales”, can lead to confusion and inefficiency. This reflects the growing shift towards “outcome-based” hiring for leaders, focused on clear results over simply time in the office.
A well-defined executive hiring strategy involves understanding the company's specific needs and creating an effective hiring process in a way that leads towards those key objectives. Without this clarity, startups risk hiring executives who may excel in general leadership but lack the targeted expertise required for the company's current challenges.
By adopting a strategic approach to executive hiring, startups can build a strong leadership team that drives growth and innovation, rather than merely adding impressive titles to the roster.
Common Challenges when Recruiting Executives in 2025
1. Hiring Operators Who’ve Never Enabled Top Sales Talent
Mistake: Bringing on execs who are used to managing processes, not empowering sellers. They might be great at systems and reporting, but if they’ve never built around the needs of top 1% sales talent, they’ll slow things down.
How to Avoid It: Look for execs who’ve supported or scaled elite sales teams before. Ask what their top reps needed and how they delivered it. If they talk tools but not seller behavior, that’s a red flag.
2. Mistaking Charisma for Sales Leadership
Mistake: A candidate who “sounds like a closer” in interviews often wins favor, especially in companies driven by sales. But being persuasive in a board meeting isn’t the same as driving results across growth stages.
How to Avoid It: Validate performance with hard metrics. Ask for numbers: quota attainment trends, churn reduction, time-to-productivity. Backchannel references from past head of sales peers or direct reports.
3. No Defined Revenue Problem to Solve
Mistake: Companies hire a commercial leader without first identifying whether they need help with Technical to Product to Sales handoff, outbound pipeline coverage, or post-sale expansion. This creates confusion and a diluted impact.
How to Avoid It: Before you open the role, define the problem clearly. Is the a need to fix forecasting, launch sales enablement, or rebuild the go-to-market strategy? Then hire someone who’s solved that exact thing before.
4. Overvaluing “Big Logo” Résumés
Mistake: Startups often default to execs from “companies with hundreds” of reps or billions in ARR. But many of those environments had strong brands doing the heavy lifting, so the candidate might not be battle-tested in low-trust sales cycles.
How to Avoid It: Prioritize adaptability. Ask how they performed in early-stage or turnarounds. Look for people who scaled a company, not just inherited scale from a strong brand.
5. Skipping Culture Fit for Speed
Mistake: In a rush to hit revenue targets, teams skip deep alignment interviews. The result? An exec who burns out reps, introduces rigidity, or kills company goals alignment.
How to Avoid It: Run a culture loop. Have them spend time with top sales reps, RevOps, and product leads. Look for signs they ask real questions, adapt to feedback, and think like a company guy, but in the good sense.
Hire the Right Executive in 2025
Hiring an executive can be either a multiplier or a mistake. The brutal truths you just read aren’t cautionary tales. They’re operating instructions.
If you’re serious about building an executive team that drives company goals instead of derailing them, act like it. Define the role. Reference deeply. Filter for truth, not polish.
And if you’ve already made a bad hire? Fix it fast. Executives shape outcomes. Don’t let inertia shape yours.
