Two Tall Guys Talking Sales – The Four Buckets of Sales Growth with Steve Wittal

Two Tall Guys Talking Sales – The Four Buckets of Sales Growth with Steve Wittal

By Sean O'Shaughnessey

In this dynamic episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome Canadian SalesXceleration expert Steve Wittal for an in-depth look into the foundations of effective sales strategies. Steve brings decades of experience in startup advisory, sales management, and business growth, sharing a robust framework that simplifies complex growth challenges into four digestible buckets: desirability, clarity, predictability, and deliverability. If you’re a business leader looking to strengthen your sales processes, sharpen your messaging, or improve revenue generation, this conversation is a goldmine.

Key Topics Discussed

  • The Power of Leadership in Change Management (~01:02)
    Steve opens by explaining why leadership is the starting point for any growth initiative, especially when change is involved.
  • The Four Buckets Framework for Growth (~03:00)
    Steve outlines his method for diagnosing and resolving growth issues by focusing on four pillars: desirability, clarity, predictability, and deliverability.
  • Desirability and Understanding the Customer’s Pain (~04:00)
    Why identifying whether your product is a “must-have” or “nice-to-have” is critical to sales success.
  • The Importance of Clarity and Quantifying the Cost of Inaction (~06:39)
    Sean and Steve unpack how clarity in messaging and value proposition can move buyers from indecision to action.
  • Predictability, Scalability, and Sales Playbooks (~09:20)
    How aligning your sales process with the customer’s buying journey enables scale and drives predictable revenue.
  • Deliverability and the Voice of the Customer (~10:50)
    Steve emphasizes the importance of retention, early wins, and referrals as indicators that your solution truly delivers.

Key Quotes

  • Steve Wittal: “A problem well-defined is a problem half-solved. Before we prescribe, we have to truly understand.” (~02:46)
  • Kevin Lawson: “When you’ve dotted all those i’s, it makes you a market-facing product. That’s how you achieve market fit.” (~13:25)
  • Sean O’Shaughnessey: “When a customer comes to you and says, ‘Can you help me solve this?’ — that’s sales nirvana.” (~08:35)

Additional Resources

  • Connect with Steve Wittal on LinkedIn – https://www.linkedin.com/in/stevewittal/
  • Steve’s email: Steve Wittal <swittal@salesxceleration.com>

A Significant Actionable Item from this Podcast

Audit Your Sales Strategy Through the Four Buckets.
Take a moment to evaluate your organization’s performance across Steve’s four key areas:

  • Desirability: Is your product essential or optional to your buyers?
  • Clarity: Can your team articulate your value proposition in a way that resonates with prospects and highlights the cost of inaction?
  • Predictability: Do you have a repeatable sales process that aligns with how your customers buy?
  • Deliverability: Are you consistently delivering on promises and capturing client feedback to validate success?

This self-assessment will uncover gaps in your current sales approach and point to immediate areas for improvement.

Summary

Whether you’re leading a startup or managing a growing sales team, this episode delivers a concise yet powerful framework for achieving sales success. Steve Wittal’s “Four Buckets” offer practical, business acumen–driven insights that will help you reframe your growth strategy and improve every stage of your sales process. If you’re serious about improving revenue generation and becoming a trusted advisor in your client relationships, don’t miss this episode. Tune in now and transform your approach to value selling.

John Spencer Explains Scaling Sales Teams- Turning A-Player Performance into Company-Wide Success

John Spencer Explains Scaling Sales Teams- Turning A-Player Performance into Company-Wide Success

By Sean O'Shaughnessey

In this episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey sit down with John Spencer, a seasoned sales leader and founder of Clear Direction Sales Development. Together, they explore the crucial differences between growth and scale, particularly in organizations leaning too heavily on a superstar seller. If you’re leading a sales organization that relies on one standout performer—or trying to replicate success across your sales team—this is a must-listen conversation packed with real-world examples and hard-earned wisdom. The trio unpacks why scalable sales processes and strong business acumen matter far more than a single heroic quota-crusher and how to transform your entire team into a consistent revenue-generation engine.

Key Topics Discussed

  • [00:01:20] The difference between growth and scale—and why one without the other creates risk
  • [00:02:30] How over-reliance on a “super seller” can mask weak sales infrastructure
  • [00:04:00] Why building a team of B players can be the key to sales success and organizational growth
  • [00:06:00] Why your people strategy outweighs even the best sales tech or product
  • [00:09:00] How aligning your company around Ideal Customer Profiles (ICPs) and value selling accelerates performance
  • [00:11:00] Inspiring second-tier sellers to level up—and the systems that make that possible

Key Quotes

  • Kevin Lawson [00:00:00]: “What do you do when you’ve got a standout salesperson and you’re trying to scale? Today’s the day to take notes and learn from best practices—and avoid the ones that put you in a bind.”
  • John Spencer [00:01:50]: “Growth is often just out-hustling the competition. Scale is when your sales management creates repeatable success across the team.”
  • Sean O’Shaughnessey [00:04:00]: “You can’t build a company on nothing but A players. You need B players who can perform with strong sales processes—that’s how you truly scale.”
  • John Spencer [00:07:24]: “When one salesperson becomes the center of gravity, the whole company starts working for them. That doesn’t scale.”
  • John Spencer [00:10:08]: “Let’s align the organization to help the salesperson like they’re a mini-CEO. That’s how we build momentum and create sustainable revenue management.”

Additional Resources

  • Connect with John Spencer: LinkedIn Profile – John Spencer (https://www.linkedin.com/in/johnspencerinc/)
  • Company: Clear Direction Sales Development
  • Contact: Direct phone, email, and Calendly available on John’s LinkedIn

A Significant Actionable Item from this Podcast

Stop idolizing your top seller—start systematizing their success.
Identify what makes your A player successful, then document and distribute that knowledge across your sales organization. Build a repeatable process that supports B players in becoming high performers. Use Ideal Customer Profiles (ICPs), clear value propositions, and structured onboarding to reduce variance and elevate the middle 60% of your team.

Why You Should Listen to This Episode

If your company is stuck in a “hero model” of selling—where success depends on a single superstar—this episode will open your eyes to what’s truly holding your sales strategy back. With practical insights on aligning your team, refining your messaging, and unlocking scalable revenue generation, John Spencer joins Kevin and Sean in a candid conversation that blends military-grade leadership with sales precision. Whether you’re a CEO, VP of Sales, or just trying to level up your sales team, this episode is your blueprint for transitioning from hustle-based growth to process-driven scale. Don’t miss it—press play and rethink what it means to grow.

Level Up Your Sales Prospecting with Advanced Research Techniques

Level Up Your Sales Prospecting with Advanced Research Techniques

By Sean O'Shaughnessey

A shoutout to Chris Spanier and Episode #85 of the Practical, Actionable Marketing Podcast

Sales prospecting has always been a grind. What if you could cut your research time in half and dramatically improve your outreach results?

In Episode #85 of the Practical, Actionable Marketing podcast, host Chris Spanier delivers a masterclass on how to do just that. Titled “Advanced Prospecting Research Tools,” the episode is packed with time-saving techniques and tools that help sales professionals build sharper prospect profiles faster.

As someone with over four decades in sales and sales management, I believe this kind of tactical insight makes a difference. If you haven’t already, listen to the episode. Then, come back here for a quick breakdown of what Chris covered—plus a few of my thoughts.

Why Prospect Research Matters More Than Ever

In a market saturated with sales messages, relevance is your only competitive advantage. The days of blasting generic emails to massive lists are over. Today, the winners are the ones who personalize their outreach with precision—and that begins with better research.

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Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

Two Tall Guys Talking Sales – Tom Gottlieb of Berkshire Hathaway Explains How Buyers Want Growth- How Sales Leaders Can Increase Company Worth – E131

By Sean O'Shaughnessey

In this insightful episode of Two Tall Guys Talking Sales, hosts Kevin Lawson and Sean O’Shaughnessey welcome business intermediary Tom Gottlieb of Berkshire Hathaway. Tom brings decades of experience in buying, selling, and valuing businesses across the Midwest. The conversation dives deep into what truly drives the value of a company—and how sales leaders and business owners alike can prepare their organizations for a future transition. Whether you’re a business owner considering a sale or a sales executive interested in how sales performance impacts company valuation, this episode delivers invaluable guidance. It’s part education, part strategy session, and all high-value insight.

Key Topics Discussed

  • The Three Core Approaches to Business Valuation – Asset, income, and comparative market methods explained simply and practically. (04:22)
  • Preparing a Business for Sale: Lessons from Real Estate – Why “curb appeal” matters for companies and how to improve it over time. (07:36)
  • What Buyers Want: Sales Growth, Consistency, and Processes – How prospective buyers assess the health of a business beyond profit margins. (09:00)
  • The Hidden Red Flag: When the Owner Is the Only Salesperson – Risks for buyers and strategies for mitigating dependency on the founder. (13:31)
  • Leveraging AI to Gain Competitive Market Intelligence – How technology is transforming buyer and seller knowledge in M&A. (11:32)

Key Quotes

Tom Gottlieb: “Every buyer wants the same thing: a business that works without the owner. That means strong processes, steady sales growth, and predictable profitability.” (09:01)
Sean O’Shaughnessey: “So if you don’t want to stick around after the sale, then train your sales team now—and watch the value of your company go up.” (14:16)
Kevin Lawson: “Tom, every time we talk, I walk away with something new. This episode is no exception.” (11:31)
Tom Gottlieb: “Buyers rarely show up with a bag of cash. There’s a timeline. A deal doesn’t close in a weekend—it’s often a year-long journey.” (07:00)

Additional Resources

A Significant Actionable Item from this Podcast

Start documenting your sales process today.
If you are a business owner—or advise one—and the majority of revenue hinges on a single salesperson (often the owner themselves), that’s a red flag for any future buyer. Begin formalizing your sales process, distribute responsibilities among team members, and track sales metrics consistently. This improves operational resilience and significantly enhances company value in a potential sale.

Why You Should Listen to This Episode

Selling a business isn’t just about profit, perception, process, and preparedness. In this episode, Kevin and Sean extract wisdom from Tom Gottlieb that applies to any B2B organization considering an exit in the next 3 to 10 years. It’s packed with strategic takeaways, sales insights, and behind-the-scenes truths about what makes a business attractive to buyers. Whether you’re a founder, an investor, or a sales leader, this episode will reshape how you think about long-term value creation. Tune in and learn how to make your business sell-ready—starting now.

To understand if your company is doing a great job in sales, take this quick and easy assessment: https://newsales.expert/b2b-sales-capability-assessment/

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

Why Cold Calling is Dead: The Shift to Relationship-Based Selling

By Sean O'Shaughnessey

Building an effective sales pipeline requires a shift in strategy. Traditional cold calling has become increasingly ineffective, with decision-makers ignoring unsolicited calls and emails.

In the spring of 2021, Bank of America Corp.’s Merrill Lynch Wealth Management unit banned trainee brokers from making cold calls. According to the Wall Street Journal, it is hard to succeed with cold phone calls in an era when no one picks up. Merrill executives said personal referrals lead to a response around 40% of the time, but less than 2% of people who are cold-called even answer the phone.

Sales teams must adopt a more strategic approach, focusing on relationships rather than volume-based outreach. The key is leveraging existing networks to create warm introductions, significantly improving engagement rates and overall success.

Cold outreach has become expensive and inefficient, and the time spent dialing numbers, leaving voicemails, and sending emails that never get opened results in diminishing returns. Many executives no longer answer unknown calls, and email filters automatically sort cold outreach into spam. Even when messages get through, recipients are skeptical, assuming they are generated by automation rather than a genuine human connection. In reality, sales professionals must find a better way to reach their target audience.

Relationship-based selling offers a more effective alternative. Salespeople should focus on leveraging their connections instead of reaching out to strangers. This approach involves identifying key contacts who can provide warm introductions to potential prospects. These “super connectors” are individuals with strong networks and the ability to facilitate meaningful introductions. By tapping into these relationships, sales teams can bypass the skepticism associated with cold outreach and start conversations with credibility.

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The Power of Personal Branding in Enhancing Sales Productivity

The Power of Personal Branding in Enhancing Sales Productivity

By Sean O'Shaughnessey

Navigating the world of sales can sometimes feel like traversing a labyrinth. Salespeople, sales managers, and CEOs alike grapple with the challenge of increasing revenue and enhancing productivity in their sales processes. To be successful, you need more than knowledge of products and services; you need to develop trust and a strong personal brand.

Business-to-business (B2B) sales involves transferring trust from ourselves to our prospects. We trust in our products and company, but convincing prospects to share that trust is the real challenge. This trust should encompass the product, the company, and perhaps most crucially, the salesperson. Remember, B2B sales could be defined as helping prospects decide in our favor within the desired timeframe.

The key to B2B sales is developing a personal brand that inspires trust in salespeople. The salesperson’s ability to convey reliability, expertise, and credibility can significantly influence how fast a prospect invests in a product or service.

Developing a strong personal brand begins with creating a presence that signals control and understanding of the business. This can be achieved by showcasing the benefits of your product or service to your customer’s business. A straightforward way to build your brand is by seeking references from your network, former employers, and customers, and showcasing these on professional platforms like LinkedIn.

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Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

Two Tall Guys Talking Sales – Measuring Marketing Success with Amy Connor of CMO OnLoan – E126

By Sean O'Shaughnessey

Welcome back to another episode of Two Tall Guys Talking Sales with Kevin Lawson and Sean O’Shaughnessey! This week, we’re diving deep into measuring marketing effectiveness with special guest Amy Connor, founder of CMO OnLoan. If you’ve ever struggled to connect marketing strategies to real business results, this episode is for you. Grab your marketing colleague and tune in—understanding what’s working (and what’s not) in your marketing is the key to driving sales growth.

Key Topics Discussed:

  • The Importance of Measuring Marketing Performance (01:08)
    Many companies don’t effectively track their marketing impact. Amy shares how focusing on key metrics—without overwhelming dashboards—can create a direct path to success.
  • Sales and Marketing Must Be Aligned (02:09)
    Customers don’t see marketing and sales as separate—they see one company. Amy explains why integrating both functions is crucial for a seamless customer journey.
  • Why Vanity Metrics Don’t Matter (02:55)
    Impressions, clicks, and leads may look impressive, but if they don’t translate to business results, they don’t matter. Learn how to focus on meaningful data that connects to revenue.
  • The Billboard Advertising Myth (03:12)
    Can a billboard drive B2B sales? Amy and Sean discuss the realities of traditional advertising and why small businesses should think critically about marketing spend.
  • Aligning Sales Messaging with Marketing Content (05:57)
    Sales teams shouldn’t be the only ones communicating key messages. Amy shares why marketing content must reinforce what salespeople say to build trust and shorten sales cycles.
  • Tactical vs. Strategic Marketing – What’s the Right Balance? (08:29)
    Should your marketing focus on brand awareness or immediate sales action? Amy explains the difference and how to measure each effectively.

Key Quotes:

Amy Connor: “Marketing and sales are part of the customer’s journey in a united way. The customer doesn’t see ‘marketing did this and sales did that’—they see the company as a whole.” (01:45)

Sean O’Shaughnessey: “Salespeople start at a disadvantage because buyers inherently don’t trust them. That’s why marketing must reinforce their message to build credibility.” (05:40)

Kevin Lawson: “Up to 70% of the buyer’s journey happens before they talk to sales. If marketing isn’t working ahead of time, you’re already losing.” (07:52)

Additional Resources:

  • Visit CMO OnLoan for free marketing resources: www.cmo-onloan.com
  • Connect with Amy Connor on LinkedIn: Amy Connor LinkedIn
  • Listen to the first episode featuring Amy: Last Week’s Podcast: https://podcasts.apple.com/us/podcast/amy-connor-discusses-salespeople-vs-lead-generation/id1668686029?i=1000693738159

A Significant Actionable Item from this Podcast:

Audit Your Marketing Metrics
Take 30 minutes this week to assess what marketing data your company is tracking. Are you focusing on impressions and clicks or lead conversion and revenue impact? Identify one metric that directly connects marketing activity to business growth and make it your priority.

Why You Should Listen to This Episode

Marketing is more than just branding—it’s a revenue-driving function. In this conversation, Amy Connor unpacks how B2B companies can measure what truly matters, align sales and marketing, and ensure every dollar spent on marketing contributes to the bottom line. If you want your marketing efforts to drive real sales results, don’t miss this insightful discussion. Tune in now!

Two Tall Guys Talking Sales – Amy Connor discusses Salespeople vs. Lead Generation: Are You Using Your Team Wisely? – E125

Two Tall Guys Talking Sales – Amy Connor discusses Salespeople vs. Lead Generation: Are You Using Your Team Wisely? – E125

By Sean O'Shaughnessey

How do you measure the success of your sales and marketing efforts? If you’ve ever wondered whether your marketing dollars are driving revenue or if your sales team is making the most of their leads, this episode is for you. 

Kevin Lawson and Sean O’Shaughnessey sit down with Amy Connor, founder of CMO on Loan, to discuss how marketing and sales should work together for growth. Amy brings her extensive experience from Procter & Gamble, Luxottica, and other top brands to help mid-market companies build marketing confidence, align with sales, and drive measurable results.

Key Topics Discussed

  • The Basketball Analogy: Why Tracking Performance Matters (~00:01:00)
    • Just like basketball teams analyze stats post-game, businesses need to measure marketing and sales effectiveness.
  • How to Decide Between Investing in Sales or Marketing (~00:04:30)
    • Business owners often wonder whether they should put more resources into sales teams or marketing initiatives—Amy breaks it down.
  • Aligning Marketing and Sales for Lead Generation (~00:07:30)
    • Should salespeople generate their own leads, or is there a more efficient way to bring prospects to the table?
  • The Role of a Fractional CMO: How Businesses Can Engage Marketing Leadership (~00:11:20)
    • Amy explains how a fractional CMO helps companies make smarter marketing decisions without the full-time executive cost.
  • A Sneak Peek into Next Week: Measuring Marketing Effectiveness (~00:13:52)
    • Tune in next week as Amy shares the tools and strategies that help businesses track what’s working and what’s not.

Key Quotes

  • Sean O’Shaughnessey (~00:06:41):
    “So many of my clients assume that salespeople will find their own leads, but is that really the best use of their time?”
  • Amy Connor (~00:07:51):
    “Your sales team is often being asked to do too much. Something will suffer if they have to hunt for leads and nurture accounts at the same time.”
  • Kevin Lawson (~00:11:00):
    “When companies say, ‘I need more sales,’ what they often mean is, ‘I need more leads.’ But are they solving the right problem?”

Additional Resources

A Significant Actionable Item from this Podcast

Evaluate your marketing and sales alignment. Take a step back and ask:

  • Do I have a clear process for tracking where leads come from and how they convert?
  • Is my sales team spending too much time prospecting instead of closing deals?
  • Would marketing support help my business generate higher-quality leads?

If you’re not sure, it may be time to review your funnel and define a strategy that ensures sales and marketing work together—not in silos.

Why You Should Listen to This Episode

This episode is a must-listen for business owners, sales leaders, and marketing professionals looking to make smarter investments in growth. Amy Connor shares real-world insights on how marketing can drive measurable business results and how sales and marketing can function as a united force. Plus, next week’s episode will dive even deeper into how to measure marketing effectiveness, so don’t miss it!

🎧 Download now and take the first step toward a more effective marketing and sales strategy!

Two Tall Guys Talking Sales – The Death of Cold Calling and the Rise of Relationship Selling – E119

Two Tall Guys Talking Sales – The Death of Cold Calling and the Rise of Relationship Selling – E119

By Sean O'Shaughnessey

Cold calling is dead—or so claims our guest, Ben Victorica, in this thought-provoking Two Tall Guys Talking Sales episode. Hosts Kevin Lawson and Sean O’Shaughnessey dive deep with Ben into the challenges of modern sales pipelines and explore why traditional outreach methods are no longer effective. Together, they uncover how relationship selling, fueled by emotional intelligence and strategic connections, is reshaping the future of sales. Whether you’re a seasoned sales professional or just starting out, this episode is packed with actionable insights you can’t afford to miss.

Key Topics Discussed

  • Why Cold Calling is Ineffective Today
    Ben discusses the inefficiency of cold outreach in the modern era, citing Bank of America’s 2021 decision to ban cold calling as a pivotal moment in sales strategy. (Approx. 00:01:00)
  • The Economics of Cold Outreach vs. Relationship Selling
    Sean explains the hidden costs of cold calling, emphasizing the expensive hourly rate of quota-bearing sales reps and its low ROI. (Approx. 00:02:20)
  • Leveraging LinkedIn for Strategic Connections
    Ben provides a practical, step-by-step guide to mining LinkedIn connections for warm referrals, using your network intelligently without costly tools. (Approx. 00:05:35)
  • The Role of Emotional Intelligence in Modern Sales
    Kevin and Ben discuss how sales professionals can use emotional intelligence and relationship intelligence tools to identify and nurture stronger business relationships. (Approx. 00:10:45)
  • Maximizing Relationship Capital with Technology
    Ben introduces KnowledgeNet, a tool that helps sales teams unlock and scale their relationship capital to drive business growth. (Approx. 00:12:00)

Key Quotes

  • Kevin Lawson:
    “Top of funnel cold outreach with no relationship is nearly impossible—it’s a cost line on any P&L.” (Approx. 00:04:48)
  • Sean O’Shaughnessey:
    “If you hand someone a list of 100 people you’d like an introduction to, you’ll get zero. But ask for five or ten, and you’ll get meaningful connections.” (Approx. 00:07:45)
  • Ben Victorica:
    “Cold calling is dead. Relationship selling instead.” (Approx. 00:01:49)

Additional Resources Mentioned

  • KnowledgeNet.ai: A powerful tool to uncover and leverage relationship capital within your organization. Visit KnowledgeNet
  • Wall Street Journal 2021 Article: Referenced by Ben regarding Bank of America’s decision to ban cold calling – https://www.wsj.com/articles/bank-of-americas-merrill-lynch-to-ban-trainee-brokers-from-making-cold-calls-11621850400.

A Significant Actionable Item from this Podcast

Use LinkedIn as a referral engine.
List key LinkedIn connections that align with your ideal customer profile. Then, approach your strongest network contacts—your “super connectors”—with a curated list of five to ten potential introductions. Respect their time and include a pre-written email template to make the referral process seamless.

Why You Should Listen to This Episode

The sales landscape has shifted, and the old playbook of cold calling no longer delivers results. This episode offers a fresh perspective on building pipelines using strategic relationships and modern tools like KnowledgeNet. Packed with real-world advice from Kevin, Sean, and Ben, this conversation will inspire you to rethink your sales approach. Ready to ditch outdated tactics and embrace the future of selling? Tune in now to gain the edge you need.

Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

Adapting to the New Sales Landscape: The Importance of Omni-Channel Outreach

By Sean O'Shaughnessey

Are you still relying on trade shows as your primary sales driver? The sales landscape has undergone a seismic shift. Those packed convention halls and endless rows of booths no longer serve as the bedrock of business development they once were.

Let’s talk about what works in today’s sales environment. Building an effective outbound pipeline isn’t just an option anymore – it’s your survival toolkit. But here’s the challenge: how do you stand out in a market where everyone’s fighting for attention?

Your unique value proposition makes all the difference. Yet many sales professionals miss a crucial point: your value proposition isn’t static. What resonates with a manufacturing client might fall flat with a distribution company. Have you tailored your message to address each industry’s pain points?

Think about your last prospecting campaign. Did you give up after four or five attempts? Research shows it takes 12 to 16 touches before prospects typically respond. This gap between persistence and practice often determines success or failure in modern sales.

The game has changed. Your prospects live in an omnichannel world. They check email between Zoom calls, scroll LinkedIn during lunch, and scan their phones throughout the day. How are you showing up in their digital world?

Consider this: every unanswered email or phone call might be a messaging problem. Are you talking about your features when you should be solving your prospects’ problems? Your prospects don’t care about your product specifications. They care about their challenges, their goals, and their bottom line.

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