Managing Freelancers and Contractors

𝗖𝘂𝗹𝘁𝘂𝗿𝗮𝗹 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝗰𝗲𝘀 𝗮𝗿𝗲𝗻'𝘁 𝗯𝗮𝗿𝗿𝗶𝗲𝗿𝘀. 𝗧𝗵𝗲𝘆'𝗿𝗲 𝗼𝗽𝗽𝗼𝗿𝘁𝘂𝗻𝗶𝘁𝗶𝗲𝘀. But only if you know how to decode them. I recently had a coaching session that highlighted this perfectly. 𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝗵𝗮𝗽𝗽𝗲𝗻𝗲𝗱: A client was struggling with her boss. The issue? Cultural miscommunication. The boss was Dutch. My client was from Asia. Two different cultural backgrounds colliding. 𝗛𝗲𝗿𝗲'𝘀 𝘄𝗵𝗮𝘁 𝘄𝗲 𝘂𝗻𝗰𝗼𝘃𝗲𝗿𝗲𝗱: 1. 𝗖𝘂𝗹𝘁𝘂𝗿𝗮𝗹 𝗖𝗼𝗻𝘁𝗲𝘅𝘁 • The boss's communication style was typically Dutch • Direct, which can seem harsh to other cultures 2. 𝗠𝗶𝘀𝗶𝗻𝘁𝗲𝗿𝗽𝗿𝗲𝘁𝗮𝘁𝗶𝗼𝗻 • My client saw it as personal criticism • In reality, it was cultural norm difference 3. 𝗧𝗵𝗲 𝗦𝗼𝗹𝘂𝘁𝗶𝗼𝗻 • Understanding the cultural context • Adapting communication styles 𝗧𝗵𝗲 𝗿𝗲𝘀𝘂𝗹𝘁? • Clarity in communication • Improved working relationship • Enhanced job satisfaction Once we put the cultural puzzle pieces in place, everything changed. My client learned to "speak Dutch" professionally. The takeaway? Cultural intelligence isn't just nice to have. It's a critical tool for career success. 𝗪𝗮𝗻𝘁 𝘁𝗼 𝗱𝗲𝘃𝗲𝗹𝗼𝗽 𝘆𝗼𝘂𝗿 𝗰𝘂𝗹𝘁𝘂𝗿𝗮𝗹 𝗱𝗲𝗰𝗼𝗱𝗶𝗻𝗴 𝘀𝗸𝗶𝗹𝗹𝘀? Watch my LinkedIn Live: "Build Your Global Leadership Edge: Cultural Intelligence for Team Success" 👉 https://lnkd.in/e3udvtik Learn how to turn cultural challenges into career opportunities. Now, I'm curious: Have you ever had an "aha" moment about cultural differences at work? Share your story in the comments. Let's build our collective cultural intelligence together. 𝗣.𝗦. 𝗧𝗵𝗶𝗻𝗸 𝗮𝗯𝗼𝘂𝘁 𝗮 𝘁𝗶𝗺𝗲 𝘄𝗵𝗲𝗻 𝘆𝗼𝘂 𝗺𝗶𝘀𝗶𝗻𝘁𝗲𝗿𝗽𝗿𝗲𝘁𝗲𝗱 𝘀𝗼𝗺𝗲𝗼𝗻𝗲'𝘀 𝗮𝗰𝘁𝗶𝗼𝗻𝘀 𝗱𝘂𝗲 𝘁𝗼 𝗰𝘂𝗹𝘁𝘂𝗿𝗮𝗹 𝗱𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝗰𝗲𝘀. 𝗛𝗼𝘄 𝗱𝗶𝗱 𝘆𝗼𝘂 𝗿𝗲𝘀𝗼𝗹𝘃𝗲 𝗶𝘁? 

The Cost of Miscommunication: How to Set Clear Expectations with VAs Miscommunication with VAs isn’t just frustrating – it’s costly. You think you’ve clearly outlined the task. They think they understand it. But somewhere along the way, the message gets lost. The result? Missed deadlines, inconsistent work quality, and endless follow-up messages. At HelpFlow, we’ve learned that the root of these issues often boils down to unclear expectations. Here’s the 3-Step Framework we use to prevent miscommunication and set VAs up for success: 1. Define the Desired Outcome – Not Just the Task Most instructions focus on the ‘what’ – the specific task to be done. Instead, start with the end goal. What does success look like? Task-Only Approach: “Update the CRM.” Outcome-Based Approach: “Move all leads from the last 30 days into the ‘Contacted’ stage. Highlight any with a follow-up date in the next week so the sales team can prioritize outreach.” Why? When VAs understand the desired outcome, they can make decisions aligned with that goal – without constant clarification. 2. Break It Down Into Actionable Steps Avoid vague instructions like “Clean up the report.” Instead, outline clear, actionable steps that leave no room for interpretation: Step 1: Download the Q1 report from [specific location]. Step 2: Cross-check revenue figures against the CRM data. Step 3: Highlight discrepancies in red and summarize them in the ‘Notes’ section. Pro Tip: Use bullet points or numbered lists to structure the task. This way, VAs can easily follow along and tick off completed steps. 3. Anticipate Potential Roadblocks VAs may hesitate to ask questions, especially when working remotely. Reduce friction by preemptively answering common questions: If data is missing: “If you can’t find specific data, check the email archive under ‘Q1 2025 Reports’ or contact [specific person].” If they’re unsure about formatting: “Use the ‘Monthly Report Template’ located in the shared Google Drive.” If deadlines shift: “If the report isn’t ready by the deadline, notify the team in Slack and update the CRM status to ‘Pending.’” Framework in Action: Here’s how we implement this at HelpFlow: - We use our AI Interviewer to capture the ‘why’ behind each task, not just the ‘what.’ - Our Task Brief Templates convert vague instructions into clear, step-by-step processes that align with the desired outcome. - VAs have instant access to a knowledge base that addresses common questions, reducing back-and-forth and keeping work moving forward. What’s one task you delegated recently that didn’t go as planned? Share it below, and let’s break it down using this framework.

Are you hiring #freelancers or independent contractors? Great! I curate and look through 100 freelance opportunities every week — so I've seen the good, great, and horrible offerings out there. If you want to attract phenomenal freelancers to partner with, then you need to include these details in your listings: 1️⃣ Your budget. Include your hourly or per-project budget or a range of rates you can pay. "$30-$60 an hour depending on experience." 2️⃣ How you pay. Are you net-30 or net-60? Any information you can include about payment methods is crucial. If a freelancer has to wait a month or more to get paid for their work, they probably aren't going to want to work with you. 3️⃣ Scope of work. The more details you can provide about what you're looking for and the problems you face the better. How long do articles need to be? How many social media videos need to be edited per week? Scope of work helps freelancers evaluate the worth of a project — and ascertain whether the budget matches the proposed scope of work. 4️⃣ How to contact you. This sounds obvious, but a lot of people hiring will say "DM me" when their DMs aren't open. Some people don't include contact information at all! 5️⃣ When you need applications by. Are you hiring ASAP? Do you have a date you need to kick off the project by? Include that information. 6️⃣ Your budget. Did you notice that I included this twice? That's because I know a lot of you will say that you prefer freelancers to send their rates over. But here's what you don't realize: your lack of transparency is costing you. Freelancers know that brands have a budget. Frankly, it sounds as though you are just looking for the lowest rate possible. Freelancers see right through that. Not to mention that even in freelancing, a pay gap exists. If you want to pay people fairly (and you should!) then you need to start including pay in any job listing — full-time, freelance, and part-time.

Here’s the mistake that I made as a beginner that cost me more than $10,000 Getting clients, closing them, and getting them results. These are all essential pillars that freelancers & businesses know. But a key factor that is often missed: Communication. I lost a client worth $10k because of miscommunication. And here are 3 things, you should learn from it: 1- Connect your client at least 4 times a month Keeping that communication flow intact, helps you understand and relate to their pain points. 2- Reiterate your scope of work This is important because both of you need to be aligned on it. This sets the client’s expectations in a correct manner. 3- Communicate both your wins & mistakes to your client Wins are of course something that is shared, but your mistakes should also be discussed. So that you can show how you’re going to improve the next time. After we fixed these, we increased our retainership by 80%. Do you have similar learnings? Let’s talk👇🏻

The labor shortage in IT field services continues to be the top concern for service leaders. We continue to see more individuals leaving the profession than entering it, and the skill gap widens. Yet, we continue to see a record number of individuals interested in independent contracting, many with decades of experience. Their motivations vary from wanting to pick up one or two jobs to building their own services business. Regardless, what they look for in the companies they work for is consistent: 1. Fair pay.   2. Clear and concise communication. In most instances, companies focus on pay and place less attention on how they structure their work orders. But in many ways, it's the communication that matters most. It clarifies for the tech what you're looking for, who you're looking for, and what it takes to get a 5-star rating. In the rare instances where there is an issue, miscommunication is often to blame. 1. Be concise. Remember, most techs are viewing your request on a phone. Our Marketplace Director put it best - think noun/verb. (ie. Router Install). 2. Be specific:  Is there a dress code? Required tools? Check-in/check-out procedures? Don't assume, tell. 3. Be consistent: Develop and use a standard work order format that is used consistently by your organization. 4. Be reachable:  Provide a reliable escalation contact to providers on-site and respond to their needs and questions promptly. Most field techs take great pride in their work, and they will seek out companies where the communications set them up for success.  

Quick tip for hiring better freelancers from places like Upwork and Fiverr. I just tried this week, and it's already been so much better. A lot of business owners know what needs to be done, but we don't have the time to be telling each person every single task along the way. And a lot of us can also slow things down because there's a lot to be done, and we don't actually know where to start. So this week, I needed a freelancer to do some work in cleaning up our CRM, and I didn’t want to deal with the usual hassle. Here's what usually happens: freelancers submit their proposals, we go back and forth, and then it turns out they can't do what they promised. So, you find another freelancer. And it takes forever to get a project done and find someone who is capable. This time, I did something different. Instead of picking the best proposal, I took a few of the top ones and asked them to create an audit/game plan for what I needed. I paid them to create this audit/game plan. This way, I could learn quickly if they're a good fit to work together. I could see things like: • How the freelancer communicated. • How they handled things when I didn't break down every single step for them • How thorough they were • How knowledgeable they are • How they asked questions on getting direction if they got stuck. And it saved me a lot of time, and prevented me from being the roadblock It’s a small upfront investment that pays off big by ensuring you get the right person for the job. I got quality of many different kinds. And it made it so much easier to pick the ones I want to work with moving forward.

As an EY Partner, I gave feedback to thousands. Master the art of feedback - skyrocket your leadership: Bad feedback creates confusion. Good feedback sparks growth. Use the CSS (Clear, Specific, Supportive) framework to make your feedback land without friction. No more awkward silences or sugarcoating disasters: 1. Give positive feedback that actually feels valuable. ❌ Don’t say: “Great job!” ✅ Instead say: “Hey [Name], I really liked how you [specific action]. It made a real impact on [outcome]. Keep doing this—it’s a game-changer.” Why it matters: → Reinforces what actually works 2 Address underperformance without demotivating. ❌ Don’t say: “You need to improve.” ✅ Instead say: “I appreciate your effort on [project]. One area to refine is [specific issue]. A great way to improve would be [solution or resource]. Let’s check in next [timeframe] to see how it’s going.” Why it works: → Pinpoints the issue without personal criticism 3. Redirect someone without crushing their confidence. ❌ Don’t say: “This isn’t what I wanted.” ✅ Instead say: “I see where you were going with [work]. One way to make it even stronger is [specific suggestion]. What do you think about this approach?” Why it works: → Keeps feedback constructive, not critical 4. Push back on an idea (without sounding like a jerk). ❌ Don’t say: “I don’t think this will work.” ✅ Instead say: “I see the thinking behind [idea]. One challenge I foresee is [issue]. Have you considered [alternative approach]? Let’s explore what works best.” Why it works: → Keeps it a discussion, not a shutdown 5. Handle conflict without escalating it. ❌ Don’t say: “You’re wrong.” ✅ Instead say: “I see it differently—here’s why. Can we walk through both perspectives and find common ground?” Why it works: → Creates space for solutions, not arguments 6. Help someone level up their leadership. ❌ Don’t say: “You need to be more of a leader.” ✅ Instead say: “I see a lot of leadership potential in you. One way to step up is by [specific behavior]. I’d love to support you in growing here—what do you think?” Why it works: → Focuses on potential, not deficits 7. Coach someone who is struggling. ❌ Don’t say: “You need to step up.” ✅ Instead say: “I’ve noticed [specific challenge]. What’s getting in the way? Let’s find a way to make this easier for you.” Why it works: → Focuses on support, not blame 8. Give feedback to a peer without sounding like a boss. ❌ Don’t say: “You should have done it this way.” ✅ Instead say: “I had a thought—what if we tried [alternative]? I think it could help with [goal]. What do you think?” Why it works: → Encourages shared ownership of improvement 9. Close feedback on a high note. ❌ Don’t say: “Just fix it.” ✅ Instead say: “I appreciate the work you put in. With these adjustments, I know it’ll be even better. Looking forward to seeing how it evolves!” Why it works: → Ends on a motivating note — ♻️ Repost it to help others grow.

This is how I've found hundreds of the best freelancers in e-commerce. I’m sharing my entire process for finding & vetting great freelance talent. After going through this, you’ll be able to find & vet the best, completely on your own, without ever having to rely on Upwork, a job posting, or staffing agency again. Here’s the process (I go into a lot more detail in the video): Step 1: Get LI Sales Navigator Easily use their search filters to find relevant talent in your space. Doesn’t matter if they have a full-time job; you’d be surprised at how many have the bandwidth to freelance. Step 2: Reach out to 10-15 prospects with a simple message: "Hi, I'm [name], founder of [company]. We're looking to improve our efforts in [channel] and your background in the space looks incredible. Would you be open to a 15 min intro call to see if it would be a good fit for you to support our team on a fractional / consulting basis?" Step 3: Have a quick intro call Don’t use this as an opportunity to interview them. Instead, share more about yourself & your company, and learn a bit about what they’re looking for. The entire goal here is to see if they’d be open to freelancing with you. Step 4: Schedule an interview Ask questions about: Trends in their area of expertise Results they’ve driven in their past (be sure to drill down and figure out what exactly THEY did vs. others on their team) Step 5: Do a paid sample project Please don’t skip this step. Have them do a paid sample project (audit, email design, strategy deck, etc) that’s directly relevant to the work they’d do if they were hired. Compensate them $300-$500 for their time. Look for: - Do they ask good, clarifying questions about the project? - Do they clarify timeline and due date? - Do they hit that timeline and due date? - Did they go "above and beyond" in the quality of work? - Did the output far EXCEED your expectations? If you see any red flags, don’t make the hire. Step 6: Make the hire! That’s the process. It’s certainly time-intensive, but like anything else, effort is needed to get great results. You can replicate this process for any hire your make, freelance or full-time. This is how I got the first 100+ freelancers for The Starters, and how you can find great freelancers without breaking the bank.

💥 Feedback is a gift they say. But only if you trust the messenger. Too many leaders confuse sharing their opinions of your actions as feedback, and when it’s critical, they might remain silent. But silence doesn’t build trust. Accountability does. If you want a practical way to give feedback that builds clarity and connection (not conflict), try the SBI+A Method: Situation, Behavior, Impact — plus Action. It’s my favorite feedback framework and it can be used for affirmative AND constructive feedback for peers, your teams and your leaders. Here’s how it works, with real-life prompts you can use today - 💬 S.B.I.+A : 🟪 SITUATION Anchor the conversation in time and place. Be specific so the context is clear. -“In yesterday’s 1:1 with the client…” -“During our team meeting this morning…” 🟧 BEHAVIOR Describe exactly what was said or done — only what you observed. Keep it neutral, which can help to de-personalize the message. - “…you rolled your eyes when Marcus offered his idea…” - “…you proactively prepared a visual to explain …” 🟨 IMPACT Here’s the heart of the conversation. Focus on the effect, not your assumption about their intent. - “…it shut down the conversation and made it harder to hear different viewpoints.” - “...it strengthened the presentation and built client confidence in our work.” 🟦 ACTION (this optional, but powerful IMO) Suggest what to change — or what to continue if it was positive. This is also an opportunity to invite the recipient of constructive feedback to share what actions they will take in light of this feedback. Sometimes, this is best delivered in a follow-up conversation after the recipient has had time to process the feedback. - “In the future, try pausing before responding so we hold space for full ideas.” - “Keep doing that — your clarity helped move the project forward.” ---------- 💡 I think this model is helpful for people-centered, equity-driven leadership because: *It builds a shared language to talk about harm, even when it’s unintentional. *It helps us shift from blame to growth — perfect for leaders trying to close the gap between intent and impact. *It makes feedback feel actionable instead of personal. And most importantly, when done well: it gets everyone back on the same page!