While I know you've already accepted a solution, here's a different approach.
I generally follow what @GonzaloMedina did with regard to defining \part and \section. But I took a very different approach with the remainder. Instead of working with a redefinition of \subsection, I decided to create two list environments that could be nested within each other. The primary reason to consider this approach is that you may actually have some other use for \subsection in your document that you don't want to tinker with.
Here's a MWE:
which produces
\documentclass{article} %% create the trainee signature and date box \newsavebox{\traineesignaturebox} \savebox{\traineesignaturebox} {\setlength{\fboxsep}{0pt}% \renewcommand{\arraystretch}{1.25}% \fbox{% \begin{tabular}{cc} \rule{0pt}{3ex}\\\hline Trainee & Date \end{tabular}}} %% you don't want this box interfering with and width, hence %% the use of `\llap`. Also, you don't want it interfering %% with vertical spacing, hence `\smash`. \newcommand{\traineesignature}{\llap{\smash{\usebox{\traineesignaturebox}}}} %% Instead of redefining subsection (since you might want those for %% another purpose in your document, create two lists to be nest. %%----------------------------------------------------------------- %% Here we create various lengths for structuring the outer most list. %% These lengths are probably not necessary. But, originally, I thought %% you might want access to their values from within the inner list. \newlength{\checklistlabelsep} \newlength{\checklistlabelwidth} \newlength{\checklistitemindent} \newlength{\checklistleftmargin} %% setting the lengths \setlength{\checklistlabelsep}{1em} \setlength{\checklistitemindent}{2em} \setlength{\checklistlabelwidth}{2em} \setlength{\checklistleftmargin} {\dimexpr\checklistitemindent +\checklistlabelwidth -\checklistlabelsep +\wd\traineesignaturebox -\checklistitemindent} %% The outer list should work like an `enumerate` environment %% so I created a counter. \newcounter{traineeCheckListCounter} \newenvironment{traineeCheckList} {\begin{list} {\traineesignature\rule{0pt}{4ex}% \makebox[\checklistlabelwidth][r]{\large\bfseries\upshape\arabic{traineeCheckListCounter}.}} {\usecounter{traineeCheckListCounter} \setlength{\labelsep}{\checklistlabelsep} \setlength{\itemindent}{\checklistitemindent} \setlength{\labelwidth}{\checklistlabelwidth} \setlength{\leftmargin}{\checklistleftmargin} \setlength{\itemsep}{\baselineskip} \setlength{\topsep}{\baselineskip} } } {% \end{list} } \newcommand{\divisionalCategory}[1]{\item {\large\bfseries\upshape #1}} \newcommand{\intermediaryCategory}[1]{\vspace{1ex}\par\hspace*{3em}{\bfseries\upshape #1}\par} %% This is the inner list. %% This list should behave more like an `itemize` list. \newenvironment{traineeAccomplishmentList} {\begin{list} {} { \setlength{\labelwidth}{1cm} \setlength{\labelsep}{1em} \setlength{\leftmargin}{\dimexpr1cm+1em} \setlength{\itemindent}{0pt} } } {\end{list}} %% From the inner list you want to create some spaces %% for checking things off. `\item` is not happy with %% a `\rule` being passed through its optional argument %% so I save this rule to a box to get around this issue. \newsavebox{\checkoffBox} \savebox{\checkoffBox}{\rule[-0.4pt]{1cm}{0.4pt}} \newcommand{\accomplishment}{\item[\usebox{\checkoffBox}]} %%-------------------------------------------------------------------------------- %% You still need a means of creating your `part` and `subparts` %%-------------------------------------------------------------------------------- \usepackage[explicit]{titlesec} \titleformat{\part} {\normalfont\LARGE\bfseries\filcenter} {\partname \ \arabic{part}:} {0.5em} {#1} \titleformat{\section} {\normalfont\Large\bfseries} {} {0.5\wd\traineesignaturebox} {\arabic{part}.\thesection\hspace*{1em}#1} %%-------------------------------------------------------------------------------- %% You need header and footers %%-------------------------------------------------------------------------------- \usepackage{lastpage} \usepackage{fancyhdr} \pagestyle{fancy} \renewcommand{\headrulewidth}{0.4pt} \renewcommand{\footrulewidth}{0.4pt} \lhead{} \chead{} \rhead{} \lfoot{7.1.2013} \cfoot{Introductory Training} \rfoot{Page \thepage\ of \pageref{LastPage}} %% These next two lines are here just for development purposes. %% \usepackage{showframe} \usepackage{lipsum} \begin{document} \part{Personnel Introduction} \lipsum[1] \section{Division Personnel} \begin{traineeCheckList} \divisionalCategory{Headquarters}\par A brief description of what this is about followed by a list of accomplishments to be named. \begin{traineeAccomplishmentList} \accomplishment first \accomplishment second \intermediaryCategory{Headquarters Administration} \accomplishment another \accomplishment and more \end{traineeAccomplishmentList} \divisionalCategory{Production Department} \begin{traineeAccomplishmentList} \accomplishment A \accomplishment B \accomplishment Lorem ipsum dolor sit amet, consectetuer adipiscing elit. Ut purus elit, vestibulum ut, placerat ac, adipiscing vitae, felis. Curabitur dictum gravida mauris. Nam arcu libero, nonummy eget, consectetuer id, vulputate a, magna. Donec vehicula augue eu neque. \accomplishment C \accomplishment D \end{traineeAccomplishmentList} \end{traineeCheckList} \end{document}
