Jason Lemkin + Kyle Norton CRO Owner: “Why Revenue Leaders Must Run Toward Bad News” (Video + Podcast)

Revenue leadership has a funny paradox: the better you are at spotting problems early, the more time you spend talking about problems. Not because you’re a pessimistbecause you’re a professional. In a conversation that’s been making the rounds in SaaS circles, SaaStr founder Jason Lemkin joined Kyle Norton (CRO at Owner.com) to unpack board dynamics, executive trust, and the uncomfortable skill that separates “solid” CROs from truly durable ones:

Running toward bad news. Not away from it. Not around it. Not into a spreadsheet bunker where you “just need a week” to clean up the forecast.

This article breaks down the core lessons from that Video + Podcast conversationthen translates them into practical moves revenue leaders can actually use: what to say, when to say it, how to bring solutions, and how to keep credibility when the quarter starts wobbling like a shopping cart with one tragic wheel.

What “Run Toward Bad News” Really Means (And What It Doesn’t)

Let’s get one thing straight: “Run toward bad news” doesn’t mean broadcasting doom on Slack like a town crier. It means you treat negative signals as actionable data instead of a personal insult.

• It means: You surface issues early, clearly, and with a plan.
• It means: You prevent “surprises” at the board meeting (because board meetings are not surprise parties).
• It means: You trade a short-term awkward conversation for long-term trust.
• It does not mean: Panic, blame, or vibes-based forecasting.

Boards, CEOs, and executive teams can handle bad quarters. What they don’t handle well is bad quarters plus late disclosure plus “we thought it would work out” energy. If you want to be viewed as a leader (not a liability), you don’t hide the smokeyou grab the extinguisher and call the fire department while it’s still one room, not the whole building.

The 8 Big TakeawaysWith Real-World Translation

1) Stop Worrying You’re Going to Lose Your Job

A lot of revenue leaders operate like they’re one bad month away from getting launched into the sun. The fear is real, but it often leads to the exact behavior that creates risk: sandbagging, overpromising, and playing defense instead of running the play.

Translation: The board usually wants stability. Replacing a CRO or VP Sales is disruptive, expensive, and risky. What they’re measuring is less “Did you hit the number perfectly?” and more “Do we trust you to tell us what’s real and steer through it?”

Practical move: Have an explicit conversation with your CEO about role evolution. In growing companies, roles shift. Sometimes a new layer appears above you. That’s not automatically a failureit can be a stage change. Leaders who discuss this proactively don’t get blindsided later.

2) Run Toward Bad News

This is the headline lesson for a reason. If you’re going to miss the quarter, you don’t wait until the board deck is printed (or worse, until the board meeting Q&A) to reveal it. You communicate early, with specifics, and with a plan.

Translation: The “bad news” isn’t just the miss. The real bad news is loss of trust. Trust is the currency that buys you time to fix things. Lose it, and suddenly everything becomes harderbudgets, headcount, strategy bets, your ability to recruit, and your CEO’s confidence in your operating cadence.

Practical move: The moment you see a credible risk, do three things within 48–72 hours:

• Name the issue: What changed? Pipeline slip? Deal pushed? Conversion dropped? Churn spike?
• Quantify impact: “If nothing changes, we miss by X.”
• Propose a plan: 2–3 options with tradeoffs (not a single “Hail Mary”).

3) Appeal to Every Board Member

Boards are rarely a single personality. You may have operators who want commit accuracy and funnel mechanics. You may have financial or brand-focused members who like logos, narrative, and market positioning. You may have investors who want crisp answers and zero surprises.

Translation: Your job is to speak “multi-board-lingual.” You can’t present one set of metrics that only makes sense to one board archetype. You need a balanced story: numbers + confidence + constraints + what you need from them.

Practical move: Build a board pack that has:

• One-page executive summary: what changed, what’s true, what’s next
• Funnel integrity: coverage, stage conversion, slippage, sales cycle changes
• Customer reality: retention, expansion, top reasons deals are won/lost
• Requests: intros, hiring help, pricing feedback, strategic calls

4) Never Play the Blame Game

It’s tempting to point at product, marketing, pricing, or “the market” when things go sideways. Sometimes those factors are real. But a revenue leader who leads with blame looks like someone who can’t control their own function.

Translation: Boards don’t expect perfection; they expect ownership. You can absolutely describe cross-functional constraintsjust don’t use them as an excuse. The fastest way to lose credibility is “It’s not my fault.” The fastest way to build it is “Here’s what’s happening and what I’m doing about it.”

Practical move: Use this language pattern:

• State reality: “We’re seeing X in the funnel.”
• Own the outcome: “Revenue is accountable for the number.”
• Describe constraints neutrally: “Product changes may impact conversion; here’s the mitigation.”
• Show competitive edge: “We can outperform by improving onboarding time, pricing packaging, or win-rate in Segment A.”

5) The Board Will Talk About You…But Not How You Think

Yes, boards discuss executives. That’s normal. But the conversation isn’t usually “How do we replace you?” It’s often “Do we feel confident?” and “Is this person seeing what’s real?”

Translation: Your job is to create confidence through clarity. When you bring hard truths early, plus a plan, you don’t look weakyou look like the adult in the room.

Practical move: When you share setbacks, pair them with:

• What you learned (not just what went wrong)
• What’s changing (process, enablement, ICP focus, pricing, qualification)
• What to watch next (leading indicators that show the fix is working)

6) Prioritize Quality Over Speed in Hiring

When you’re behind plan, the instinct is to hire fastmore reps, more managers, more “please fix it.” But rushed hiring often creates a second problem: underperformers who require months of management time, distract the org, and dilute culture.

Translation: A mediocre hire can cost you more than an empty seat, especially in leadership roles. The pipeline doesn’t magically improve because your org chart looks busier.

Practical move: If you must hire quickly, tighten the profile instead of loosening it. Focus on:

• proven motion fit (PLG, sales-led, enterprise, SMBwhatever you actually run)
• evidence of coachability and process discipline
• clear performance data (not just “great storyteller” interviews)

7) Due Diligence Is CrucialFor Candidates and CEOs

This one is spicy and practical: before taking a CRO/VP Sales role, ask for real artifactsboard materials, pipeline hygiene, churn realities, how decisions get made. “Trust me” is not a metric.

Translation: Great revenue leadership is context-dependent. Some companies are set up to win. Some are set up to chew through CROs like a subscription service for executive burnout.

Practical move: Revenue leaders evaluating a role should ask:

• What are the last 2 quarters’ forecast accuracy and why?
• What’s churn and top churn drivers?
• What’s the real ICP and who closes best?
• What does the CEO believe about sales? (This matters more than the comp plan.)

8) Keep Good People in Your Corner

In tech, relationships are leverage. The right mentors, peers, and internal allies help you think, decide, and recover faster when things get messy. The wrong people help you…decorate the deck while the ship is taking on water.

Translation: If you find people who genuinely care, keep them close. Invest in them. Promote them. Build your “career board of directors” the same way you build a company board: thoughtfully.

A Mini Playbook: How to Run Toward Bad News Without Face-Planting

Step 1: Separate “Signal” From “Noise”

Bad news usually whispers before it screams. Your job is to listen early. Common early indicators:

• late-stage deals stalling (“legal review” becomes “legal vacation”)
• conversion drops at a single stage
• sales cycle extending by even 10–15%
• pipeline quality deterioration (more “maybe” deals, fewer “must win”)

Step 2: Diagnose the Root Cause (Not the Symptom)

“Pipeline is light” is a symptom. Root causes include ICP drift, weaker qualification, pricing packaging mismatch, onboarding friction, or competitive pressure in a segment you shouldn’t be in anyway.

Quick test: Ask, “If we doubled pipeline tomorrow, would we close more…or just lose faster?” If the answer is “lose faster,” your fix is not “more pipeline.”

Step 3: Communicate EarlyWith Options

When you escalate bad news, don’t bring a problem-shaped mystery box. Bring choices.

Example message (short and human):

• Reality: “We’re tracking a likely 8–10% miss unless we change course.”
• Why: “Late-stage slippage is up, mostly in Segment B; win-rate down 6 points.”
• Plan A: “Re-focus on Segment A, tighten qualification, shift enablement.”
• Plan B: “Pull forward expansion plays, short-term pricing incentives with guardrails.”
• Ask: “We need help with 5 intros in vertical X and approval to pause two hires.”

Step 4: Make “No Surprises” an Operating System

The best board updates are boring in the best way: clear, consistent, and never shocking. Create a cadence:

• weekly CEO revenue brief (10–15 minutes)
• board member check-ins ahead of meetings when needed
• one shared scoreboard of leading indicators (not 47 dashboards, just the truth)

Specific Examples: What This Looks Like in Real Revenue Life

Example 1: The “We Might Miss” Quarter

It’s week 6 of the quarter. Your forecast says you’re fine. Your gut says the forecast is lying. Three big deals are “90%” but none have confirmed security timelines. The worst move is to pray. The best move is to run toward it:

• Re-forecast with a “commit confidence” score based on verifiable steps.
• Tell the CEO: “We have a confidence gap; here’s the math.”
• Bring a mitigation plan: focus reps on 10 expansion accounts, pull in exec sponsors, tighten close plans.

You might still miss. But you won’t be surprised. And neither will the board.

Example 2: The Temptation to Blame Product

Demo-to-close conversion drops after a product change. It’s real. But if you march into the meeting saying “Product broke sales,” you’ve already lost half the room.

Better framing: “We’re seeing conversion friction post-change. Revenue owns the number; here’s the customer feedback, the mitigation, and where product and revenue are aligned on the fix.”

Example 3: Hiring Under Pressure

You’re behind. The CEO wants 10 reps. You know the enablement and pipeline can support 6. Running toward bad news means saying the hard thing:

“If we hire 10 now, we’ll create 10 ramp problems and dilute coaching. If we hire 6 with a higher bar, we can keep quality and hit productivity targets.”

Why This Topic Hits So Hard Right Now

Revenue leadership today is more complex than “hire reps, set quotas, celebrate.” Boards want predictability. Markets shift. Buyers are skeptical. And with AI tooling changing workflows, leaders are being asked to understand systemsnot just results.

In that environment, running toward bad news becomes a competitive advantage. The companies that win aren’t the ones that never struggle; they’re the ones that surface reality quickly, decide cleanly, and execute without theater.

Field Notes: of Real-World “Running Toward Bad News” Experiences

Below are experiences that revenue leaders commonly describe when they adopt (or resist) the “run toward bad news” mindset. Think of these as realistic vignettes from the CRO/VP Sales trenchesanonymized patterns, not fairy tales.

Experience 1: The Quarter You Save by Admitting You’re in Trouble

A CRO notices something subtle: pipeline coverage looks normal, but late-stage deal momentum is off. Sales calls sound “positive,” yet the next steps are vague. Instead of waiting for the forecast call, the CRO pulls a 48-hour audit: every late-stage deal gets a written close plan with dates, stakeholders, and a clear “why now.” The result is uncomfortable: several deals were never real commitsjust optimistic placeholders. The CRO tells the CEO early, reframes the quarter with a conservative commit, and immediately reallocates effort to high-intent expansions and faster-moving segments. The team still feels the pressure, but the company avoids the bigger disaster: being blindsided at quarter-end. The CEO later describes the moment as the turning point where they started trusting the revenue org’s numbers again.

Experience 2: The Board Meeting That Goes Well Because the Bad News Went First

A VP Sales learns a lesson the hard way: boards hate surprises. The next time churn creeps up, the VP doesn’t bury it on slide 27. They lead with it. First slide: “Churn is up 1.8 points QoQ. Here’s why, what we’ve done in two weeks, and what we need help with.” The weird part? The board becomes calmer. The conversation shifts from “Why didn’t you tell us?” to “How can we help?” A board member offers two customer intros for win-back. Another suggests a pricing packaging change based on portfolio experience. The meeting still has tensionbut it becomes useful tension, not defensive tension.

Experience 3: The Career Boost That Comes From Taking the Hit, Not Dodging It

A CRO inherits a mess: inconsistent qualification, sloppy handoffs, and a “big pipeline” that’s mostly vibes. When the quarter starts failing, the CRO could blame history: “I just got here.” Instead, they take ownership: “This is where we are, and I’m responsible for the fix.” They implement tighter stage definitions, retrain managers on deal inspection, and publish a weekly scoreboard of leading indicators. The number still misses that quarterbut the organization finally understands why, and the next quarter improves. Ironically, the miss doesn’t hurt the CRO’s reputation; the clarity helps it. Leadership isn’t about never missing. It’s about being the person everyone trusts when things get real.

Experience 4: The “Bad News” That Prevents a Bad Hire

Hiring pressure makes people do silly thingslike hiring a leader who interviews well but can’t run the motion. A revenue leader senses a finalist doesn’t have true experience with the company’s ICP and sales cycle. The “bad news” is awkward: the CEO is excited, the candidate is charismatic, and everyone wants the seat filled yesterday. Running toward bad news means saying: “I don’t think this person will work here, and here’s the evidence.” The team slows down, reopens the search, and eventually hires someone less flashy but far more effective. Six months later, the revenue leader realizes the hard conversation didn’t slow the company downit prevented months of cleanup.

Closing Thoughts

If you’re a revenue leader, your job is not to be the hero who magically makes every quarter perfect. Your job is to create truth, build trust, and drive decisions. “Run toward bad news” is the operating principle that makes all three possible.

Because here’s the secret: bad news doesn’t disappear when you ignore it. It just gets promoted…into worse news.