Elea CareyCommunications pro; life amateur, but improving
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In this order: Mom, sober alcoholic, seasoned businessperson, writer, compassionate bitch.



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Other very experienced answerers have offered helpful practical advice, including tools. I will add the one thing I think matters and needs to be understood and communicated before you decide tools and processes: What are your company values? My response is based in over thirty years of watching both remote and local teams struggle profoundly with communication and the documentation of knowledge (which is kind of like the library/archive of those communications). In instances where communication in all its forms (live and as an archive) failed, it was because the team did not know or was not fully bought into the values of the company. In instances where I've seen companies succeed, it's been because all stakeholders were deeply invested in the core values of the enterprise and consciously checked all their actions to ensure they were consistent with those shared and dearly held values. I encourage my C-suite & founder advisees to define their values with their team, share those values in an introduction and ongoingly, and establish a periodic check-in timeline for making sure the people, products and customer experience are aligned with those values. When you have those things in place, you can then check the tools you're considering to determine if they are appropriate for the environment you're nurturing. If you'd like to talk with me about how to find your company's values, communicate them to your team, and established systems to ensure their alignment, please let me know.


This question has generated such interesting discussion (I love it when Clarity members answer by consciously building on each other's replies). I've been watching founders launch and raise and fail to raise and fail and launch again for over three decades in every ecosystem from publishing to VC. I'm going to share this from my experience: What if those stories of raising and launching that look successful from the outside or seemed to be easy were actually just very well orchestrated announcements of what was years of hard work and much failure? Because that is very often the case: Those of us who are not in the sausage factory while the sausage is being made only get to see that yummy, perfect-looking piece of sausage served up on a platter of gold with all the right fixins. But what preceded that perfect moment was all manner of behind-the-scenes chaos and blood and guts and gore and loud machinery and overworked factory employees and don't forget the part about when the lease was suddenly up and the sausage had to be made out of garbage cans in the founder's ex-girlfriend's basement and so on. That's an extended sausage metaphor but you get it: it wasn't actually easy. So then the question for you, dear asker, becomes, What if YOU stop believing that raising is remarkably easy for some and crazy hard for others?



What has been most helpful to me in both my personal and business life is to surrender to the idea that none of us is an individual acting in an individual manner but instead we are all engaged in a dynamic and we each have a role. If that is a way of thinking you are open to, I would suggest you look at what your role is in the current dynamic. My recommendation is not about blaming yourself; in fact, it's almost the opposite of blaming, because it gives you something you can make significant progress on--your personal development, your behavior change--rather than trying to change others (which is impossible) or changing the situation, which almost always leads us to having the situation arise again because we have not changed ourselves. Examining and changing ourselves is the hardest work we do, and it is the most rewarding because we have so much power in this area. If you are interested in looking at your role in this situation and discussing the slow and powerful route of changing so that your future relationships are better, please get in touch.


I'll tell you what I am right now -- Real happy I found this question. Thank you to whoever thought to ask it! Few things matter more to me than being real in myself. I struggle with that every day, running that test, or, said another way, asking that question: Am I being real right now? True to myself, not acting on my fears (even if fearful), centered, kind, thoughtful. I work to release my resentments at the end of every day and assess what I can work on tomorrow to be more present (that's what I call "really real," the ability to be present). This is the work I do with founders, C-suite businessfolk, parents struggling to maintain some balance between the realities of work and family life. If you are interested in being more "real in your self," please get in touch.


Fascinating question! And how exciting to be thinking of how you'd like to grow. My first question back to you is, rather than being "more than just a middleman," would you be willing to consider deeply refining and profiting from your role as a middleman? Not "more than," but "more of." As you already know, running a brokerage is a marvelous perspective from which to learn both sides of a marketplace. My experience of broker-modeled businesses comes from watching my father and grandfather grow their brokerage and also from my experience of supporting chambers of commerce by managing their member publications. I saw those businesses flourish from doubling down on their brokerage model, rather than seeing it as a less-than position that somehow needs to be grown beyond. For example, in my family business, we got to know both the supplier and the customer by vending hardwood lumber from sawmills to builders. We deepened those relationships by listening to the builders' needs and helping them refine what they ideally wanted from a sawmill. Then we worked with the sawmills to customize their basic products to increase sales (through us!) to the builders. My mentor in the publishing business used to say, "If you want to make money, be there when the money changes hands." In that business, we got to know our customers by selling advertising in their publications; as we listened to both the chambers on one side and the ad-buyers/members on the other, we learned what they would ideally like to get from each other. The chambers wanted stronger member relations, including publication distribution from their members, and the members wanted a wider variety of publications to advertise in, which we were only too happy to create. So the questions for you then become as much about customer relationships as about changing your business model. And the daily actions toward ideal growth have to do what how you're addressing customer relationships. What are you doing to listen to customers? What are your mechanisms for increasing dialogue, gathering customer feedback, and challenging your team to brainstorm new offerings? Above all, what are your core individual and company values and what daily actions are you taking to model and disseminate those values with your team members and customers? It would be an honor to talk with you if you'd like to discuss further.


My work has related to many aspects of the challenges of entry level jobs both from an employer perspective and from the perspective of the entry level employee. The overriding challenge for the employer, in my experience, is being able to promulgate leadership's values to new stakeholders, including, first-off, making sure they understand they are valued stakeholders. Presumably, you did not launch your business in order to live out values that are inconsistent with your own personal values. So the question you must ask yourself is, if, for example, honesty is something you value, how are you modeling that honesty beginning with your interview process and continuing with onboarding, training, managing, and promoting your employees? Staying true to your own personal core values will allow you to create a company you recognize and intuitively know how to manage and grow. That, in turn, will give you very few employees who stay at the entry-level, and more happy and engaged employees who become deeply invested team members with long-standing careers.

If you're interested in growing a business that is based in core values you're proud of and that experiences strong, healthy, sustainable growth, let's talk.


I'm sorry you're going through this! Looking back over three decades of experience, with a lot of that in early-stage companies, I'd say this is a very common growth pattern: you've come as far as you could with the early team, now you and the company are ready to challenge yourselves, and you introduce, whether consciously or not, a kind of irritant to push growth. I have been that young lady for sure, but I've also been in your role, and I've been a part of the old guard that felt the umbrage. So the question becomes, what can you do in your own thinking and then in addressing the dynamic to get the best from all for the health of the enterprise.

1) Stop-- Stop thinking there's a problem and start seeing the opportunity for what it is, a potentially alchemical relationship among seemingly unlike elements. I'm not asking you to deny there's a problem, I'm asking you to ask yourself (and therefore, your team) to look deeper.

2) Look-- Where are the fears? If they appear to be all on one side--for example, from your veterans--then you're not seeing the whole picture. Just assume that each party has equal fear and that as long as they're acting out of fear, they will see problem not opportunity.

3) Listen-- And ask your team to listen to each other, not to you, or at least not just to you. This isn't an excuse for you to abdicate and just let them figure it out. If you do that, you'll lose the opportunity to develop better leadership skills, in addition to creating more friction on the team. Instead, this is about developing more empathy, which presumably they need in their outward-facing work to understand and solve customer problems. So think of this as an opportunity for Customer Empathy 101 for the team. This is just one idea, but could be helpful. Can they see each other as potential customers, each with a need for a product or solution that only the other can provide? If that's the relationship, and the "purchase price" is a paycheck and job satisfaction, what is each team member willing to do for the customer?

Again, I'm sorry you're facing this situation. I'm sure it's both tiresome and worrisome (and plenty of other adjectives). I'm happy to spend some time on the phone if you'd like.


I'm with Janice on this one -- what is your idea of failure? And most importantly, why do you ask? I bet you've got an interesting reason. Call me if you want to discuss.


You're already nearly home if you know what you like. For process, I'd recommend running your posting wherever you want (Craigslist, freelancewriting.com, indeed.com) and soliciting test copy *in a contest.* I've done this quite successfully with designers. You will feel better about offering something in exchange for the work and you'll get a greater range of talent, since seasoned oldsters and brand newbies both like contests. I have used Submittable.com for contest submissions. Call me if you want me to lay out further or if you would like help with submissions.


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